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WORKS OF PROF. A. F. HOLLEMAN 


PUBLISHED BY 


JOHN WILEY & SONS. 


A Text-book of Inorganic Chemistry. 
By Dr. A. F. HorrEMAN, Professor Ordinarius in the 
University of Groningen, Netherlands. Rendered into 
English by HERMON C. CooPer, Ph.D., Instructor in Syr- 
acuse University, with the co-operation of theauthor. 8vo, 
viii + 458 pp., 84 figures. Cloth, $2.50. 5 


A Text=book of Organic Chemistry. 

Rendered into English from the Second Dutch Edition by 
A, JAMIESON WALKER, Ph.D. (Heidelberg), B.A., Head 
of Department of Chemistry, Municipal Technical College, 
Derby, Eng., assisted by Owen E. Morr, Ph.D. (Hei- 
delberg), Demonstrator of Chemistry, Municipal Technical 
College, Derby, Eng., with the co-operation of the author. 
8vo, xvlitsss pages, 73 figures. Cloth, $2.50. 

A companion volume to the preceding, and forming with 
it a comprehensive treatise on pure Chemistry. 


Laboratory Manual of Organic Chemistry for 
Beginners, 

An Appendix to the Author’s Text-book of Organic 
Chemistry. Translated from the Dutch by A. JAMIESON 
Wa ker, Ph.D. (Heidelberg), B.A., Head of the Depart- 
ment of Chemistry, Technical College, Derby, England. 
With the Co-operation of the Author, zr2mo, xiv +78 
pages. Cloth, $1.00 net. 





A 
LABORATORY MANUAL 


OF 


ORGANIC CHEMISTRY 
FOR BEGINNERS. 


BY 


Dr. A. F. HOLLEMAN, 


Professor Ordinarius in the University of Groningen, Netherlands, 
and Fellow of the Royal Academy of Sciences, Amsterdam. 


AN APPENDIX TO THE AUTHOR’S TEXT-BOOK OF 
ORGANIC CHEMISTRY. 


TRANSLATED FROM THE DUTCH 
BY 


A. JAMIESON WALKER, Ph.D. (Heidelberg), B.A., 


Head of the Department of Chemistry, Technical College, Derby, England. 


WITH THE CO-OPERATION OF THE AUTHOR. 


ERST EDITION. 


FIRST THOUSAND, 


NEW YORK: 
JOHN WILEY & SONS. 
LONDON: CHAPMAN & HALL, LIMITED, 
1904. 





Copyright, 1904, 
By Lae 
A. JAMIESON WAL 





(Entered at Stationers 


* 


AUTHOR’S PREFACE. 


Ir is admitted universally that chemistry cannot be learnt 
by the study of text-books only, and that laboratory practice 
is essential. A student new to the science derives most benefit 
from a laboratory course of inorganic preparations, simple 
quantitative experiments, and qualitative inorganic analysis. 
He is brought thus into contact with work closely connected 
with the text-books and lectures on this division of chemistry, 
and is enabled to understand the subject much better than by 
any other method. 

A student beginning the study of organic chemistry usually 
has to content himself with text-books and lectures, and very 
seldom has the opportunity of handling the compounds about 
which he has to read.. There is, evidently, therefore, a lack in 
the methods of teaching the elements of organic chemistry 
adopted in the Universities. 

Several years have elapsed since a course of practical work 
in organic chemistry was introduced into the Universities of 
the Netherlands, chiefly through the influence of Professor 
FRANCHIMONT of Leyden. This laboratory work is a comple- 
ment to the lectures, and has proved very satisfactory. 

At the suggestion of Dr. A. JAMIESON WALKER, the labora- 
tory manual written by me in Dutch for this purpose is issued 
now in English. At his request, I have revised the whole text, 
and added some new experiments. In most instances I have 


indicated the weights or volumes suitable for the reactions, an 
ili 


iv AUTHORS PREFACE. 


experience of many years having taught me that students 
always employ much larger quantities than are necessary. 
The amounts prescribed are approximate, and, to ensure the 
success of the experiments, need not be weighed or measured 
with great accuracy. 

It should be mentioned that this manual is related intimately 
to my text-book of organic chemistry, and constitutes an appen- 
dix to it. To obtain the maximum advantage from these ex- 
periments, I advise the student first to study them with the aid 
of the text-book, and afterwards to carry them out in the labora- 
tory. This is the only method by which he can attain to a 
thorough comprehension of his laboratory work. 

A. F. HOLLEMAN. 

GRONINGEN, NETHERLANDS, March, 1904, 


TRANSLATOR’S PREFACE. 


Durina the few months the English edition of Professor 
HorLLEMAN’s “Text-book of Organic Chemistry’’ has been pub- 
lished, it has taken a foremost place among works on the science 
for students’ use. The volume now issued constitutes an ap- 
pendix to the text-book, and forms an introductory guide to 
laboratory.work in organic chemistry, as well as a compendium 
of experiments suitable for lecture-table illustration. 

The translation is from a completely revised and consider- 
ably extended copy of the Dutch edition, specially prepared by 
Professor HOLLEMAN for the purpose. To facilitate reference, 
I have added paragraph headings, and all the manuscript and 
proof-sheets have been corrected by the author, to whom I am 
much indebted for his careful revision. 

References in the text printed in Clarendon type are to my 
translation of Professor HOLLEMAN’s “Leerboek der Organische 
Chemie,” and those to ‘Inorganic Chemistry” to Dr. Cooprr’s 
translation of his “Leerboek der Anorganische Chemie,” pub- 
lished by Messrs. JonN WILEY and Sons. 

My thanks are due to the publishers for the care they have 
bestowed on the production of the work. - 

A. JAMIESON WALKER. 


Dersy, ENGLAND, April, 1904, 
v 





CONTENTS. 


Light figures refer to pages; Clarendon figures to the author’s ‘‘ Text-book of 
Organic Chemistry.”’ 


PAGE 

I. QUALITATIVE ANALYSIS OF CARBON COMPOUNDS (8-8)......... 1 

Pteienitom 0; Carbon and Hydrogen (8)... rvi. 1 
Carbonization, 1. Oxidation with copper oxide, 1. 

B Negen (A). tn. ck sk dns ee Lae ee he oe no wl 2 


LASSAIGNE’Ss method, 2. WiLL and VARRENTRAP’S 
method, 2. KsmLpAHL’s method, 2. 


Maen marae riialoogens (BN... vante we we kaos cede wees 2 
BEILSTEIN’s test, 2. Calcium-oxide test, 3. 
NE ETCH OET ORE SAE 3 
CARIUS’ test, 3. Caustic-alkali test, 3. 
Ii. Tor ArLorroric MODIFICATIONS OF CARBON (16) ............ 4 


Graphite, 4. Wood-charcoal, 4. Bone-charcoal, 4. 
Decolourization of solutions by bone-charcoal, 4. Ab- 
sorption of lead salts by bone-charcoal, 4. Deodeuriz- 
ing action of bone-charcoal, 5. 

Pee aArORATOEny METHODS (18-27)... sene wie aen 5 

Fractional distillation, 5. Steam distillat‘on, 5. Ex- 
traction with solvents, 6. Determination of the melt- 
ing-point, 6. Determination of the boiling-point, 7. 
Crystallization, 7. 

IV. SarurRaTED HYDROCARBONS (29-42)... 20... . ccc cee eee cee ees 7 

Preparation of methane, 7. Distillation of petroleum, 

8. Inflammability of petroleum-vapour, 8. Stabil- 
ity of the saturated hydrocarbons, 8. 
Been corre eatin | OH. (48-55). o.a ae als wen ee eS 9 

Action of sodium upon alcohol, 9. Fusel oil, 9. Wine, 

9. Heat developed by mixing alcohol and water, 9. 
Test for water in alcohol,9 Separation of water from 
alcohol, 10. Oxidation of ethyl alcohol, 10. 

vii 


Vili CONTENTS. 


VI. ArkyL Hatives, Esters, AND Eruers (56-64).............. 10 
Ethyl chloride, 10. Ethylsulphuric acid, 10. Diethyl 
ether, 11. Ethylmercaptan, 12. 
VII. Amines AND NITRO-COMPOUNDS (69-77) ..........ecececcess 12 
Amines (69-74) rn. cnn on cee pa ke Bla 12 
Methylamine, 12. Carbylamine reaction, 12. Mustard- 
oil reaction, 12. Reaction with copper salts, 12. 
Nitrous-acid test, 13. Nitrosamines, 13. Dimethyl- 
amine and trimethylamine, 14. 
Nitro-compounds (75-17) 0... ses ous 0 an en 14 
Sodium nitromethane, 14. Nitrolic-acid reaction, 14. 
Reduction of nitro-compounds, 14. 


VIII. Nrrrizes ÁND ISONITRILES (83-85) ecn en 14 
Preparation, 14. Hydrolysis of nitriles, 15. 
IX. Saruratep Acips, CyHnO,; AND Esters (86-92, 91) ......…. 15 


Formic acid, 15.- Decomposition of mercuric formate, 
15. Action of concentrated sulphuric acid on formic 
acid, 16. Oxidation of formic acid by potassium per- 
manganate, 16. Cacodyl test for acetic acid, 16. 
Stability of acetic acid towards oxidizing-agents, 17. 
Silver acetate, 17. Test for acetic acid, 17. Oxidation 
of ethyl alcohol to acetic acid, 17. Saponification of 
butter, 18. Calcium and lead salts of the higher fatty 
acids, 18. Volatile fatty acids, 18. Higher fatty acids, 
18. Soap, 19. Ethyl acetate, 19. Velocity of saponi- 
fication of ethyl acetate, 19. Solubility of ethyl acetate 
in water, 19. 
X. ALDEHYDES AND KETONES (106-121). ... ennn 20 
Aldehydes (106-118) .. 0.00... 0c s cele ee 20 
Acetaldehyde, 20. Silver-mirror test, 20. Aldehyde- 
resin, 20. Scuirr’s reaction, 21. Coagulation of egg- 
albumin, 21. Action of formaldehyde on gelatine, 21. 
Ketones (106-112, 119 and 120)... . .) 0. see 21 
Acetone, 21. Test for acetone, 21. Addition-product 
of acetone and sodium hydrogen sulphite, 21. Sepa- 
ration of acetone from aqueous solution, 21. Oxida- 
tion of acetone, 22. 

XI. UnsaTuRATED HYDROCARBONS (122-184) ............se0uueee 22 
Olefines (122-129) . „it. .0, sda 22 
Kthylene, 22. Luminosity of the ethylene flame, 22. 

Action of bromine on ethylene, 22. Von BAEYER’s 


CONTENTS. ix 


PAGE 


test for the double bond, 23. Explosive mixture of 
ethylene and oxygen, 23. Unsaturated hydrocarbons 
in coal-gas, 23. Double linking in amylene, 23. 
iin A LSS) 6. cscs eft lava cds Sec eecesesedes 23 
Preparation of acetylene, 23. Copper acetylene and sil- 
ver acetylene, 23. 
XII. Monopasic UNSATURATED Acips (189-144)................ 24 
Double bond in almond oil, 24. Oleic acid from almond 
oil, 24. Elaïdie transformation, 24. Fusion of oleic 
acid with caustic soda, 24. Lead oleate, 25. 
XIII. CrrLOROFORM AND Iopororm (150-152)................... 25 
Preparation of chloroform, 25. Action of caustic potash 
on chloroform, 25. Conversion of chloroform into po- 
tassium cyanide, 25. Chloroform and silver nitrate, 
26. Iodoform test for alcohol, 26. 
RER 160) ee ter are ee see essen en 26 
Preparation of allyl alcohol, 26. Test for glycerol, 26. 
Action of alkalis on copper salts in presence of 
glycerol, 26. BAUMANN and SCHOTTEN’S test for hy- 
droxyl-groups, 27. 
XV. SATURATED Drsasic Acips (168-167) ..................... 27 
va EA DE ER EE 27 
Preparation of oxalie acid from wood, 27. Conversion 
of formates into oxalates, 27. Calcium, lead, and cop- 
per oxalates, 28. Decomposition of calcium oxalate 
by heat, 28. Decomposition of lead and copper oxa- 
lates by heat, 28. Action of concentrated sulphuric 
acid on oxalic acid, 28. Complex oxalates, 29. Di- 
methyl oxalate, 29. Diethyl oxalate, 29. Oxamide, 
29. 
ent U EE EEEN ales ols vel eters 30 
Barium succinate, 30. Basic ferric succinate, 30. Suc- 
cinimide, 30. 
XVI. Hyproxy-acips OR ALCOHOL-ACIDS (182-198) .. ..........…. 30 
EN re ele 30 
Decomposition of lactic acid by dilute sulphuric acid, 30. 
Decomposition of lactic acid by concentrated sulphuric 
acid, 30. Test for ee with phosphorus 
pentachloride, 31. 
Ode 1L92—197), eee etten e's wa ies lar delen 31 
Potassium tartrates, 31. Iron ammonium tartrate, 81. 


x CONTENTS. 


PAGE 
FEHLING’s solution, 31. Action of heat on tartaric 
acid, 32. Microchemical method of distinguishing be- 
tween tartaric acid and racemic acid, 32, ‘Tartar 
emetic, 32. 
Citric Acid. (198) 5 st a, SO By 
Preparation from lemons, 32. Action of concentrated 
sulphuric acid on citric acid, 32. 
XVIL Catoran Hypratm (204) nnn 33 
Action of water on chloral, 33. Action of caustic potash 
on chloral hydrate, 33. Silver-mirror test for chloral 


hydrate, 33. 
XVIII. ALDEHYDE AND KETONE ALCOHOLS OR SUGARS (206-231). 33 
Properties of the Monoses (208)... ..% sen ss eile een 33 


Silver-mirror test, 33. Resinification with caustic al- 
kalis, 34. Reduction of Ferurine’s solution, 34. 
Osazones, 34. 


Methods of Formation of the Monoses (210). ...........---%- 34 
Inversion of sucrose (cane-sugar), 34. Glycerose, 34. 
Pentoses (211) on oie sie ep nee 34 
Furfuraldehyde test, 34. 
Hetoses (212) … „ennn ee + ole 0 4 mle sateen 35 
Hydrochloric-acid test, 35. 
d-Glucose (212, 1)... 5. ..24. nn 35 


Calcium alkoxide of d-glucose, 35. Glucosesulphuric acid, 
35. Copper alkoxide of d-glucose, 35. Detection of 
d-glucose in urine,36. Oxidation of d-glucose by nitric 


acid, 36. 
d-Fructose (212, 2) annen 36 
Alcoholic character, 36. Test for d-fructose, 36. 
d-Galactose (212, 6) nnen nn 36 
Oxidation of d-galactose to mucic acid, 36. 
Hexodioses (215-228) 2.4... 5. <6 0 44 nn 37 
Sucrose (217-221)... 60... dee. s oes 2 oe 37 


Properties distinguishing sucrose from the monoses, 37, 
Action of heat on sucrose, 37. Tricalcium saccharate, 
37. Inversion, 37. 
Lactose (216). 05. assen 37 
Detection of lactose in milk, 37. Lactosazone, 38, 
‘“‘Sand-sugar,” 38. 
Polyoses (224-231) … 2.0 0s 0c ce En + aes toes 
Starch (226 and 227) «eiste stee selene senen enen ea ee 


CONTENTS. x1 


PAGE 
Starch-paste, 38. Properties distinguishing starch from 
the monoses, 38. Conversion of starch into d-glucose, 
38. Iodine test for starch, 38. Barium alkoxide of 
starch, 38. Conversion of starch into dextrin, 38. 
Potato-starch, 39. 
iere PAIR 39 
Hydrolysis of cellulose, 39. Parchment-paper, 39. 
Solubility of cellulose in ScHWEITzER’s reagent, 39. 
Nitrates of cellulose, 39. Detection of lignin in paper, 
40. 
XIX. Hyprocyanic ACID AND ITS SIMPLE AND COMPLEX SALTS (242 
nn A le EE 40 
Hydrocyanic acid, 40. Prussian-blue test, 40. Silver 
cyanide, 40. Hydrolysis of potassium cyanide, 41. ° 
Conversion of ammonium formate into hydrocyanic 
acid, 41. Double ferrocyanide of potassium and cal- 
cium, 41. Ferroeyanie acid, 41. Action of concen- 
trated sulphuric acid on potassium ferrocyanide, 41. 
Potassium ferricyanide, 41. Reduction of potassium 
ferricyanide, 42. Oxidation of potassium ferrocyanide 
by potassium permanganate, 42. 
XX. POTASSIUM CYANATE AND POTASSIUM THIOCYANATE (244 and 
DVS cho) AEN SL SOR Lene tes 42 
Potassium cyanate, 42. Potassium thiocyanate, 42. 
Silver thiocyanate, 42. 

XXI. DERIVATIVES OF CARBONIC Acip (248-256). ............... 43 
VOET A ORO EEE 43 
Inflammability, 48. Volatility, 43. Solvent power, 43. 

Barium trithiocarbonate, 43. Potassium and copper 
salts of xanthic acid, 43. 
ern VA Ginie EEE EEEN s maleate 44 
WOHLER’S synthesis, 44. Urea oxalate, 44. Urea 
nitrate from urine, 44. KNoP’s method for the esti- 
mation of urea in urine, 44. BuNnsEen’s method for 
the estimation of urea in urine, 44. LieBie’s method 
for the estimation of urea in urine, 44. Action of heat 
on urea, 45. Cyanuric acid, 45. 
nT TO NEEM wie ae On 45 
Calcium carbamate, 45. Ammonium dithiocarbamate, 
45. 
Remen Grour (257 and 258) … aats oenen 46 


sik CONTENTS. 


Ammonium urate, 46. Di-potassium urate, 46. Mu- 
rexide test for uric acid, 46. Reduction of silver 
nitrate by uric acid, 46. Murexide test for caffeine, 46. 
XXIII, BENZENE AND ITs HOMOLOGUES (2638-270)............... 
Stability of benzene towards the halogens, 47. Absence 
of double bonds in benzene, 47. Nitrobenzene, 47. 
Benzenemonosulphonic acid, 47. FriepeL and 
Crarts’ reaction, 47. * Formation of benzene from 
calcium benzoate, 47. Oxidation of side-chains, 48. 
XXIV. MONOHALOGEN CoMPOUNDS (272 and 278) ................ 
Stability of monochlorobenzene towards alcoholic potash 
or soda, 48. Saponification of benzyl chloride by 
caustic potash or soda, 48. Benzyl iodide, 48. 
XXV. Mononuypric PHENous (274-276). .............. een 
Preparation of phenol from calcium salicylate, 49. Prep- 
aration of phenol by fusion of sodium benzenesulpho- 
nate with caustic soda, 49. Sodium phenoxide, 49. 
Tribromophenol, 49. Ferric-chloride test for phenol, 
49. Depression of the freezing-point of phenoi, 49. 
Action of nitric acid on phenol, 50. Cresol, 50. 
XXVI. MONOAMINO-COMPOUNDS AND THEIR DERIVATIVES (282-291). 
Aniline, 50. Neutral reaction of anline, 50. Aniline 
salts, 51. Tribromoaniline, 51. Bleaching-powder test 
for aniline, 51. Potassium-dichromate test for ani- 
line, 51, Acetanilide, 51. Carbylamine reaction, 51. 
Diphenylamine, 51. Nitrosodimethylaniline, 51. Azo- 
benzene, hydrazobenzene, and benzidine sulphate, 52, 
Diphenylurea, 52. 
XXVIL Benzotc Acip AND ITS DERIVATIVES (296-298) .......... 
Benzonitrile and benzoic acid, 52. Benzoic acid from 
gum-benzoin, 53. Volatility of benzoic acid with 
steam, 53. Ethyl benzoate, 53. Benzanilide, 58. 
Benzamide, 53. Oxidation of cinnamic acid by potas- 
sium permanganate, 54. 
XXVIII. BENZALDEHYDE' (299). .....250.5 504 9 ere en ee 
Silver-mirror test, 54. Benzaldehydephenylhydrazone, 
54. Sulphite compound of benzaldehyde, 54. Action 
of alcoholic potash on benzaldehyde, 54. Oxidation of 
benzaldehyde by potassium permanganate, 55. 
XXIX. Diazonium CoMPOUNDS AND AZO-DYES (302-304, and 320— 
824) ores clock or te cuneate 


PAGE 


48 


49 


50 


52 


54 


CONTENTS: xl 


PAGE 
Benzenediazonium chloride, 55. Replacement of the 
N,-group in benzenediazonium chloride by hydroxyl, 
55. Diazoaminobenzene, 56. Aminoazobenzene, 56. 
Dyeing with aminoazobenzene, 56. Reduction of 
aminoazobenzene, 56. Oxidation of phenylhydrazine 
by Frexuurne’s solution, 56. 
XXX. POLY-SUBSTITUTED DERIVATIVES NG SIMILAR SUB- 
TECH ES PE 57 
Pyrogallol, 57. Benzoquinone, 57. Tests for catechol, 
resorcinol, and quinol, 57. m-Dinitrobenzene, 57. 
Test for nitrous acid with m-phenylenediamine, 58. . 
Phthalic anhydride, 58. Fluorescein, 58. Phenol- 
phthaleïn, 58. Red anion, of phenolphthalein, 58. 
XXXI. PoLy-suBSsTITUTED Derrvatives CoNTAINING Two or Morr 
DISSIMILAR SUBSTITUENTS (382-851) ................ 59 
p-Diazobenzenesulphonic acid, 59. Nitrophenols, 59. 
Picric acid, 59. Potassium picrate, 59. Taste of 
picric acid, 59. Dyeing with picric acid, 60. Iso- 
purpuric acid, 60. Chloropierin, 60. Ionization of 
picric acid in aqueous solution, 60. Salicylic acid, 60. 
Action of bromine-water on salicylic acid, 60. Iden- 
tification of salicylic acid and phenol, 60. Calcium 
salicylate, 60. Action of tannin on gelatine, 60. 
Test for tannin, 60. Action of tannin on quinine, 61. 
Interaction of albumin and tannin, 61. Hydrolysis 
of p-nitraniline hydrochloride, 61. 
XXXII. TERPENES AND CAMPHORS (358-368)... ................ 61 
Artificial camphor, 61. Volatility of camphor with steam, 
61. Camphor and water, 62. Camphoric acid, 62. 
XXXII. BENZENE-NUCLEI LINKED TOGETHER BY CARBON (864— 
ie Er gee ae Ai eran sy we giehe a ane he ee 62 
Rosolic acid, 62. Magenta, 62. Action of concen- 
trated hydrochloric acid on a solution of magenta, 62. 
Colour-base, 62. Leuco-base, 63. 
XXXIV. CONDENSED BENZENE-NUCLEI (370-885) ............ Oe 
Action of heat on naphthalene, 63. Naphthalene pi- 
crate, 63. Naphthalenemonosulphonic acid, 63. a- 
Nitronaphthalene, 63. Crude naphthol, 63. Martius’ 
yellow, 63. Naphthylamines, 64. Congo-red, 64. 
Naphthionic acid, 64. Oxidation of anthracene by chro- 
mic acid,64. Test for anthraquinone, 64. Alizarin, 64, 


Xiv CONTENTS. 


XXXV. HeETEROCYCLIC Compounns (386-394) ................0-- 
Pyridine, 65. Action of pyridine on ferric chloride, 65. 
Test for pyridine, 65. Action of the alkaloid-reagents 
on pyridine, 65. Stability of pyridine towards von 
BAEYER’s reagent, 65. Stability of pyridine towards 
oxidizing-agents, 65. Pyrrole-red, 65. Indophenin 
reaction, 66. Tests for antipyrine, 66. 
XXXVI. CONDENSATION-PRODUCTS OF BENZENE AND HETEROCYCLIC 
Nucrer (895-899)... noor 
SKRAUP’s synthesis of quinoline, 66. Quinoline hydro- 
chloride, 66. Quinoline picrate, 66. Quinoline di- 
chromate, 67. Volatility of indigo, 67. Solubility of 
indigo in nitrobenzgne, 67. Indigosulphonic acid, 67. 
Oxidation of indigo toisatin, 67. ‘‘Indigo-vatting,” 67. 
XXXVI. Atkators (400-411) 2.1.0.0. ee 
Alkaloid-reagents, 67. Nicotine, 67. Fluorescence of 
quinine-sulphate solution, 68. Action of chlorine on 
quinine salts, 68. Test for strychnine, 68. Test for 
brucine, 68. 
XXXVIIL Atsumins (412-418) 20. ar on Soin ce eee 
Detection of nitrogen and sulphur in the albumins, 68. 
‘‘Salting-out’’ albumin with ammonium sulphate, 68. 
Coagulation of albumin by alcohol, 69. Coagulation 
of albumin by nitric acid, 69. Biuret reaction, 69. 
Minion’s reagent, 69. Xanthoprotein reaction, 69, 
ADAMKIEWICZ’s reaction, 69, Decomposition-products 
of ceratin, 69, 


66 


67 


68 


A LABORATORY MANUAL OF 
ORGANIC CHEMISTRY. 


I. QUALITATIVE ANALYSIS OF CARBON COMPOUNDS. 
(3-8.) 


DETECTION OF CARBON AND HYDROGEN (3). 


1. Carbonization.—A small quantity of sugar is heated in a 
crucible covered with a lid. Inflammable gases are evolved, 
leaving a residue of charcoal. This is proved to be carbon by 
heating it in a hard-glass tube about 15 cm. long sealed at one 
end, and slightly inclined, the tube being first filled with oxy- 
gen, and closed with a loosely-fitting cork. Carbon dioxide is 
formed, part remaining in the tube. After cooling, lime-water 
is agitated with the gas, and becomes turbid owing to the forma- 
_ tion of calcium carbonate, CaCQ,. 

The presence of carbon in coal-gas is shown by the soot 
deposited when a cold surface, such as that of a porcelain cru- 
cible-lid, is introduced into a luminous flame. | 

2. Oxidation with Copper Oxide.—10 g. -of finely-powdered 
copper oxide—a hygroscopic substance—are dried by heating 
in a dish or crucible. While still warm it is mixed carefully 
with a small quantity of sugar, and the mixture placed in a 
hard-glass tube sealed at one end; the open end of the tube is 
then closed with a cork, and a delivery-tube leading into lime- 
water. On heating, the sugar is oxidized by the copper oxide; 


2 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


the carbon dioxide evolved makes the lime-water turbid, and 
the water formed condenses in drops on the cool part of the tube. 


DETECTION OF NITROGEN (4). 


3. a) LASSAIGNE's Method.—A piece of dried albumin—a 
substance containing nitrogen—and a piece of sodium are placed 
in a narrow tube sealed at one end. The tube is then gradually 
heated to redness, and maintained at this temperature for a 
short time. The hot end of the tube is placed in 2-3 e.c. of - 
water, whereupon it cracks, and the sodium cyanide formed 
dissolves. After filtering through a small filter-paper, and 
washing the residue with a few drops of water, a drop of a solu- 
tion containing iron in the ferrous and ferric states is added to 
the filtrate, and the mixture acidified slightly with hydrochloric 
acid to dissolve the precipitated ferrous and ferric hydroxides. 
If sodium cyanide was present, there remains a blue precipitate, _ 
due to the formation of Prussian blue. 

b) WILL and VARRENTRAP’S Method.—Small pieces of dry 
albumin are mixed with five times their bulk of soda-lime, and 
the mixture warmed in a test-tube. A strip of moist, red lit- 
mus-paper held at the open end of the tube is turned blue by 
the evolved ammonia, and the characteristic odour of the gas 
can also be detected. | 

c) KJELDAHL’s Method.—0-1 g. of acetamide is heated with 
2 e.e. of concentrated sulphuric acid in a test-tube. After a 
short interval, the reaction-mixture is poured carefully into 
25 c.c. of water, excess of caustic soda added, and the beaker 
covered with a glass plate having a moistened strip of red litmus- 
paper adhering to its lower surface. In a few minutes the lit- 
mus is turned blue by the evolved ammonia. 


DETECTION OF THE HALOGENS (5). 


4. a) BEILSTEIN’s Test.—Copper oxide is introduced into 
a loop at the end of a piece of platinum-wire by dipping the 


QUALITATIVE ANALYSIS OF CARBON COMPOUNDS. 3 


moistened loop into finely-powdered copper oxide, heating in 
the flame, and repeating these operations several times. A 
piece of copper-oxide wire held by the platinum-wire can also 
be used. The copper oxide is then heated to redness until the 
flame is no longer coloured, cooled, moistened with a drop of 
chloroform, CHC], by the aid of a capillary pipette, and again 
introduced into the flame. The vapour of the copper halide 
(chloride) formed imparts a fine green colour to the flame. 

b) Calcium-oxide Test.—A lump of quicklime is heated in a 
test-tube to a high temperature, and, while still hot, two drops 
of chloroform are added. When cold, the contents of the tube 
are treated with water, and the lime dissolved by dilute nitric 
acid free from hydrochloric acid. On addition of silver nitrate 
to this solution, a precipitate of silver chloride is obtained, prov- 
ing the presence of chlorine in the chloroform. 

Chloroform is agitated with silver-nitrate solution, but no 
precipitate of silver chloride is formed. 


DETECTION OF SULPHUR (5). 


5. a) CARIUS’ Test.—0-1 g. of ammonium thiocyanate, 
NH,CNS, is warmed with 5 c.c. of nitric acid of 1-2 specific gray- 
ity till the reaction begins; to prevent the oxidation becoming 
too violent, the heating is then discontinued. After dilution 
of the cold solution with 25 c.c. of water, barium chloride 
is added, the resulting white precipitate of barium sulphate 
indicating that the sulphur has been oxidized to sulphuric 
acid. 

b) Caustic-alkali Test.—Some albumin is warmed with 
concentrated caustic-soda solution (1:2), in which it dissolves, 
forming sodium sulphide among the products. This can be 
proved either by adding a few drops of lead acetate, resulting in 
the formation of black lead sulphide, PbS; or by bringing a 
drop of the liquid into contact with a bright silver coin, with 
production of a brownish-black stain of silver sulphide, Ag,S; 


4 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


or by addition of two or three drops of a solution of sodium 
nitroprusside to the alkaline mixture, when a deep-violet colour- 
ation results, some minutes elapsing before the colour attains 
its maximum intensity. Traces of sulphur can be detected by 
this reaction. 


II. THE ALLOTROPIC MODIFICATIONS OF CARBON. 
(16.) 


1. Graphite.—0-1 g. of graphite is mixed with 5g. of finely- 
powdered copper oxide, and heated to a high temperature in 
the apparatus described in I, 2. The evolved carbon dioxide 
renders the lime-water turbid. 

2. Wood-charcoal.— A piece of wood-charcoal is gently 
heated in a test-tube; the water occluded in the pores of the 
charcoal evaporates, and condenses in drops on the cool parts 
of the tube. 

A piece of wood-charcoal is placed in water, and the mixture 
warmed. The air present in the pores of the charcoal escapes, 
forming bubbles in the water. 

3. Bone-charcoal.—Pieces of bone are placed in a crucible 
fitted with a lid, and heated in a fume-cupboard. Vapours of 
disagreeable odour are evolved, the residue in the crucible 
consisting of bone-charcoal and the mineral constituents of 
the bones. The bone-ash is freed from these by heating the 
mixture with hydrochloric acid. 

4. Decolourization of Solutions by Bone-charcoal.—20 c.c. 
of a very dilute solution of magenta—a red dye—are agitated 
with a teaspoonful of bone-charcoal, and filtered. The filtrate 
is colourless (‘Inorganic Chemistry,” 177). 

5. Absorption of Lead Salts by Bone-charcoal.—20 c.c. of a 
very dilute solution of lead acetate are tested for lead by addi- 
tion of an aqueous solution of sulphuretted hydrogen. The 
solution must be so dilute that it gives a brown turbidity, but 
no precipitate. | 


LABORATORY METHODS. 5 


A like volume of the lead-acetate solution is agitated for a 
short time with a teaspoonful of bone-charcoal, and then fil- 
tered. On addition of sulphuretted-hydrogen water, no tur- 
bidity or brown colouration is developed in the filtrate (‘‘Inor- 
ganic Chemistry,” 177). 

6. Deodourizing Action of Bone-charcoal.—A dilute aqueous 
solution of sulphuretted hydrogen, having a perceptible odour 
of the gas, is agitated with bone-charcoal, and filtered. An 
odourless filtrate is obtained. 


III. LABORATORY METHODS. 
(18-27.) 


1. Fractional Distillation—50 c.c. of rectified spirit are 
placed in a 100-c.c. fractionating-flask fitted with a thermo- 
meter and connected with a condenser, and gently heated with 
a small flame. The liquid begins to boil about 78°, and the 
distillate is collected in two fractions, the first passing over 
below 88°, and the second above that temperature. After the 
distillation is complete, the first fraction is returned to the flask, 
and slowly distilled till the thermometer again reaches 88°. 
The burner is then removed, the second fraction poured back 
into the flask, and the distillation continued without changing 
the receiver till the temperature has again risen to 88°. A dif- 
ferent receiver is now employed, and the process continued till 
distillation is complete. 

The first fraction contains most of the alcohol, and can be 
ignited; the second is chiefly water, and is incombustible. 

2. Steam Distillation.—100 c.c. of petroleum are placed in a 
200-c.c. flask d (Fig. 1) connected with a condenser. Water is 
boiled in the can a, which is fitted with a safety-tube b and a 
delivery-tube c, the evolved steam being passed into the flask d 
through a glass tube reaching to the bottom, and bent as in the 
illustration. The flask is inclined at an angle to prevent the 


6 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


petroleum being carried over mechanically. The distillate is a 
mixture of petroleum and water. 


7 | ¢ 







































































































































































1.—Steam Distillation. 





3. Extraction with Solvents.—10 c.c. of a five per cent. solu- 
tion of urea and 10 e.e. of ether are introduced into a separating- 
funnel, and the mixture vigorously shaken. When the liquid 
has separated into two layers, these are removed, and each is 
evaporated to dryness in a porcelain dish on the water-bath. 
Only a trace of urea is obtained from the ether, this substance 
being very soluble in water, and almost insoluble in ether. 

A saturated solution of salicylic acid is prepared by vigor- 
ously agitating 1 g. of the acid with 25 c.c. of water, and filter- 
ing. The filtrate is extracted with 10 c.c. of ether as described 
in the last paragraph. Almost all the salicylic acid dissolves in 
the ether, being very soluble in this solvent, and but slightly 
soluble in water. 

4. Determination of the Melting-point.—A little naphtha- 
lene is placed in a narrow glass tube sealed at one end, several 


*. 


SATURATED HYDROCARBONS. 7 


of these being obtained by drawing out a test-tube. The capil- 
lary tube is fastened with an india-rubber ring to the stem of 
a thermometer, so that the part containing the naphthalene is 
about half-way up the mercury bulb. The end of the ther- 
mometer carrying the tube is then immersed in a beaker of water, 
which is slowly heated with a small flame. When the sub- 
stance melts, the temperature (80°) of the thermometer is 
observed. 

5. Determination of the Boiling-point.—A small quantity of 
benzene is placed in a fractionating-flask having a high side- 
tube connected with a condenser. The flask is closed with a 
cork fitted with a thermometer whose bulb is placed several 
centimetres below the side-tube. The benzene is heated with a 
small flame to ebullition, and the temperature at which the 
mercury becomes stationary noted. ‘This is the boiling-point. 

6. Crystallization.—3 g. of crude oxalic acid are dissolved 
in 10 e.e. of hot water, and the impurities present in the acid 
removed by filtering the turbid solution. On standing, the 
clear filtrate deposits crystals of oxalic acid. The mother- 
liquor is poured off, the crystals are drained on a funnel, and 
dried on a porous plate or between sheets of filter-paper. 


IV. SATURATED HYDROCARBONS. 
(29-42.) 


1. Preparation of Methane, CH,—One part by weight of 
sodium acetate, which has been fused and finely powdered, is 
thoroughly mixed with four parts by weight of soda-lime. The 
mixture is heated in a hard-glass retort of 100 e.c. capacity, 
fitted with a delivery-tube for collecting the gas in cylinders 
over water. Methane thus prepared always contains some 
hydrogen, and to obtain a product of maximum purity, it is 
best to keep the temperature as low as possible. A thick- 
walled cylinder is filled with methane, closed with a glass plate, 


8 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


and turned mouth upwards. On removal of the cover, and 
ignition of the gas with a burner or taper, it burns with a flame 
of feeble luminosity. When combustion ceases, some lime- 
water is poured quickly into the cylinder, the cover replaced, 
and the contents agitated. The carbon dioxide formed by the 
combustion of the gas renders the lime-water turbid. 

A thick-walled explosion-cylinder is filled about one-third 
full with methane, and the remainder with oxygen. On igni- 
tion, the mixture explodes with a loud report. 

A eylinder is filled with chlorine by downward displace- 
ment, and over it is placed an inverted cylinder full of methane, 
closed with a glass plate. The plate is removed, and the gases 
mixed by inverting the cylinders several times, care being taken 
to prevent loss. After insertion of two glass plates between the 
cylinders, one is placed mouth downwards in a saturated so- 
lution of common salt, and the cover removed. In diffused 
daylight the liquid slowly rises, the colour of the chlorine dis- 
appears, and oily drops of the substitution-products—methyl- 
ene chloride, CH,Cl,; chloroform, CHCl,; and carbon tetra- 
chloride, CCl,—are deposited on the sides of the cylinder. The 
mixture must not be exposed to direct sunlight, or there is danger 
of an explosion. On ignition of the contents of the other cylin- 
der, hydrochloric acid is produced, and soot deposited. 

2. Distillation of Petroleum.—Petroleum is distilled slowly 
from a flask connected with a condenser and fitted with a ther- 
mometer. The boiling-point rises gradually, proving the liquid 
to be a mixture. 

3. Inflammability of Petroleum-vapour.—5 c.c. of petroleum 
are poured into a porcelain dish. A lighted match plunged 
into the liquid is extinguished. If, however, the petroleum is 
carefully heated to 40° on a water-bath, the inflammable vapour 
evolved is ignited by the application of a burning match. 

4. Stability of the Saturated Hydrocarbons.—Samples of 
petroleum and of paraffin-wax are agitated with concentrated 
sulphuric acid and with concentrated nitric acid. Being mix- 


ALCOHOLS. 9 


tures of saturated hydrocarbons, they are neither acted on nor 
dissolved. 


V. ALCOHOLS, C,H,,.,-OH. 
(43-55.) 


1. Action of Sodium upon Alcohol.—0-5 ¢. of sodium is intro- 
duced into a small fractionating-flask containing 10 c.c. of abso- 
lute alcohol, and fitted with a delivery-tube for collecting gas 
over water. The mouth of the flask is immediately closed with 
a cork, and an energetic evolution of gas takes place. The gas 
is collected in a cylinder, and proved by ignition to be hydro- 
gen. 

2. Fusel-oil.—aA small quantity of crude spirit is evaporated 
slowly on a water-bath. After the volatilization of the ethyl 
alechol, the odour of fusel-oil is very marked. It is also per- 
ceptible when a few drops of the spirit are placed on the palm 
of the hand, and rubbed with the finger to promote the evapo- 
ration of the ethyl alcohol. 

3. Wine.—25 c.c. of wine contained in a fractionating- 
flask connected with a condenser are heated on a water-bath. 
Alcohol distils. and can be recognized by its odour and in- 
flammability. 

4. Heat Developed by Mixing Alcohol and Water —10 cc. 
of absolute alcohol and 10 ¢.c. of water are poured into two small 
beakers, and these immersed in a large vessel of water to bring 
them to the same temperature. This is noted, and after re- 
moval of the beakers from the water their contents are mixed 
quickly and stirred with the thermometer. A rise in temper- 
ature is observed. 

5. Test for Water in Alcohol.—3 g. of blue. crystallized copper 
sulphate CuSO,+5H,O are gently heated in a porcelain cruci- 
ble tili anhydrous the salt being converted into a white powder. 
When cold, the residue is transferred to a test-tube or small 


IO =A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


flask containing 15 e.e. of aqueous alcohol; the copper sulphate 
soon regains its original blue colour, on account of the forma- 
tion of the hydrated salt, CuSO,+ 5H,0. 

6. Separation of Water from Alcohol.—Rectified spirit is 
agitated with solid potassium carbonate, and, if enough of the 
salt has been added, two layers are obtained. ‘These are sep- 
arated by means of a tap-funnel. The upper layer is strong : 
alcohol, and burns on ignition; the lower layer is a concen- 
trated, aqueous solution of potassium carbonate, containing 
only a trace of alcohol. 

7. Oxidation of Ethyl Alcohol.—Ethy] alcohol is heated with 
an aqueous solution of potassium permanganate until the violet 
colour has disappeared and manganese dioxide has been pre- 
cipitated. On acidifying the mixture with sulphuric acid and 
distilling, an acid distillate with an odour of acetic acid is ob-_ 
tained. 


VI. ALKYL HALIDES, ESTERS, AND ETHERS. 
(56-64.) 


1. Ethyl Chloride.—A mixture of 10 e.e. of aleohol and 5 c.c. 
of concentrated sulphuric acid is added to 5 g. of common salt 
contained in a 50-c.c. fractionating-flask connected with a con- 
denser in a fume-cupboard. On warming, gaseous ethyl chloride, 
C,H,Cl, is evolved, and dissolves in the condensed alcohol. 
When ignited, this distillate burns with a green, flame—a phe- 
nomenon characteristic of many chlorine derivatives. The pres- 
ence of chlorine can also be proved by BEILSTEIN’s test (I, 4a). 

2. Ethylsulphurie Acid About 2 c.c. of concentrated sul- 
phuric acid are poured carefully into an equal volume of absolute 
alcohol, the mixing being accompanied by rise of temperature. 
The mixture is heated gently for a short time, cooled, and poured 
into 25 c.c. of water This solution is stirred, and barium car- 
bonate added till the liquid is no longer acid to litmus. Carbon 
dioxide is evolved, with formation of insoluble barium sulphate 


BERNE HALIDES, ESTERS, AND ETHERS. II 


and soluble barium ethylsulphate, Ba(C,H,SO,),. After filter- 
ing, dilute sulphuric acid is added to a portion of the filtrate; 
the precipitate of barium sulphate formed proves the presence 
of a barium salt in solution. 

On warming the rest of the filtrate with dilute hydrochloric 
acid, barium sulphate is precipitated. This is due to the de- 
composition of the liberated ethylsulphuric acid into alcohol 
and sulphuric acid, followed by the interaction of the latter 
with the barium ions present in the solution. 

3. Diethyl Ether, (C,H;),0.—A fractionating-flask is fitted 
with a cork carrying a tap-funnel and a thermometer, both 
arranged to nearly touch the bottom. After 50 c.c. of alcohol 
of ninety per cent. strength and 50 e.e. of concentrated sul- 
phurie acid have been poured into the flask, it is connected with 
a condenser through whose jacket a rapid current of water is 
flowing. Heat is then applied till the thermometer indicates a 
temperature between 130° and 140°. As soon as the distillation 
of ether begins, alcohol is introduced slowly into the flask from 
the tap-funnel, and the distillation continued with a small 
flame so as to maintain the temperature constant. The distil- 
late is agitated in a separating-funnel with a like volume of 
water, which dissolves most of the alcohol, leaving a layer of 
ether floating on the surface of the solution. After separation 
from the latter, the ether is dried by agitation for a few minutes 
with fused and finely-powdered calcium chloride. 

A small quantity of the ether is agitated with a large excess 
of water, in which it dissolves. 

A mixture of 5 ¢.c. of ether and 5 c.c. of water is shaken in a 
separating-funnel, and the ethereal and aqueous layers sepa- 
rated carefully. Anhydrous copper sulphate added to this 
ether turns blue, proving that the ether has dissolved some of 
the water. On gently warming the aqueous layer in a porcelain 
dish, ether-vapour is evolved, and can be recognized by its 
odour and inflammability. This proves that the water has dis- 
solved some of the ether, 


12 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


A few drops of ether are poured into a porcelain dish and 
ignited, a very luminous flame being obtained. 

The absorption of heat caused by the evaporation of ether can 
be demonstrated by placing a small quantity in the palm of the 
hand, and blowing on it. A sensation of cold is felt immediately. 

4. Ethylmercaptan.—On warming 2 c¢.c. of a saturated 
solution of potassium ethylsulphate with a like volume of a 
thirty-three per cent. solution of potassium hydrogen sul- 
phide, KHS, the odour of ethylmercaptan at once becomes 
perceptible (66). 


VII. AMINES AND NITRO-COMPOUNDS. 
(69-77.) 
AMINES (69-74). 


1. Methylamine.—A thin paste of bleaching-powder is ren- 
dered strongly alkaline by addition of slaked lime, and mixed 
with an aqueous solution of 1 g. of acetamide, CH,-CONH,. 
On distillation, an aqueous solution of methylamine, CH,-NH,, 
is obtained (244). 

2. Carbylamine Reaction.—A portion of the solution thus 
obtained is warmed gently with one or two drops of chloroform 
and a small quantity of alcoholic potash. Owing to the forma- 
tion of methylearbylamine, CH,-NC, the odour characteristic of 
isonitriles is perceived (84). 

3. Mustard-oil Reaction.—A mixture of carbon disulphide 
and absolute alcohol in like proportions is added to another 
portion of the distillate obtained in 1, till solution is complete, 
and the liquid is warmed for a short time. On addition of ferric 
chloride, a black precipitate of sulphide of iron is formed; and, 
on further heating, the odour of methyl-mustard-oil, CH,-NCS, 
becomes perceptible (254). | 

4. Reaction with Copper Salts.—The remainder of the dis- _ 
tillate of 1 is added drop by drop to a dilute solution of copper 


AMINES AND NITRO-COMPOUNDS. 13 


sulphate. At first a precipitate of copper hydroxide is formed, 
and, on further addition of the amine-solution, this redissolves, 
with production of a deep-blue colour. The reaction, therefore, 
is analogous to that between ammonium hydroxide and copper 
salts (‘Inorganic Chemistry,” 244). 

5. Nitrous-acid Test.—A concentrated aqueous solution of 
1 g. of ethylamine hydrochloride, C,H;NH,-HCl, and 1 g. of 
potassium or sodium nitrite is poured slowly through a thistle- 
funnel into a 50-e.e. fractionating-flask a, containing 20 c.c. of 
glacial acetic acid (Fig. 2). The evolved nitrogen is freed from 





















































Fra. 2.—Nitrous-acid Test for Primary Amines. 


traces of ethyl nitrite by passing it through a small wash-bottle 
b, containing alcoholic potash. The gas is collected over water 
in a cylinder c, and proved to be nitrogen by its extinguishing 
a lighted wood-splint or taper. By means of the iodoform test 
(XIII, 5), the presence of alcohol in the fractionating-flask can 
be shown. 

6. Nitrosamines.—To a cold, saturated, aqueous solution of 
1 g. of potassium or sodium nitrite is added 1 g. of solid diethyl- 
amine hydrochloride, (C,H;),.NH’HCl, and one drop of dilute 
sulphuric acid. On gently heating the liquid, diethylnitros- 
amine, (C,H,;),N-NO, collects on the surface as a yellow oil of 
characteristic odour (72). 


I4 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


7. Dimethylamine and Trimethylamine.—A small quantity 
of caustic-soda solution is added to herring-brine contained in a 
distilling-flask connected: with a condenser. On heating, a dis- 
tillate is obtained; this is alkaline, owing to the presence of 
dimethylamine and trimethylamine. Like ammonium hydrox- 
ide, it precipitates ferric hydroxide, Fe,O,+nH,O, from a solu- 
tion of ferric chloride. 


NITRO-COMPOUNDS (75-77). 


1. Sodium Nitromethane.—A solution of 3 drops of nitro- 
methane in 1 c.e. of absolute alcohol is prepared. To this are 
added a few drops of a solution of sodium ethoxide, obtained 
by dissolving small pieces of sodium in 10 e.e. of absolute alco- 
hol. The white precipitate of sodium nitromethane is filtered 
off, and, while still moist, is dissoived in a small quantity of 
water. Jt must not be dried or a dangerous explosion may result. 
When moist, it is innocuous. 

2. Nitrolic-acid Reaction.—The liquid thus obtained is agi- 
tated with a few drops of a concentrated aqueous solution of 
sodium nitrite, and carefully acidified with dilute sulphuric 
acid. On addition of dilute caustic-soda solution, a blood-red 
solution of the sodium salt of methylnitrolic acid is produced. 

3. Reduction of Nitro-compounds.—To caustic potash and 
granulated zine contained in a test-tube are added 3 drops of 
nitromethane. The characteristic odour of methylamine at 
once becomes perceptible, and a strip of red litmus-paper held 
in the vapour is turned blue. 


VIII. NITRILES AND ISONITRILES. 


(83-85.) 


1. Preparation —A mixture of 10 g. of potassium ethyl- 
sulphate and 10 g. of dried potassium ferrocyanide is submitted 
to dry distillation in a retort connected with a condenser. The 


SATURATED ACIDS AND ESTERS. 15 


distillate has the isonitrile odour, due to the presence of ethyl- 
carbylamine. Agitation with dilute sulphuric acid for a short 
time removes this smell, whereupon that of the nitrile—pro- 
pionitrile—formed in the reaction becomes perceptible, although 
it was previously wholly masked by that of the isonitrile, a by- 
product. 

2. Hydrolysis of Nitriles——The liquid of 1 is made alkaline 
with caustic potash, and boiled in a test-tube. The evolution 
of alkaline vapours can be detected by means of a strip of moist- 
ened, red litmus-paper. : 

The reaction-mixture contains potassium propionate. On 
acidifying with dilute sulphuric acid and distilling, propionic 
acid passes over, the distillate turning blue litmus red. 


IX. SATURATED ACIDS, (,H,,0,; AND ESTERS. 
(86-92; 97.) 


1. Formic Acid.—A mixture of 10 g. of glycerol and 10 g. of 
erystallized oxalic acid is heated in a fractionating-flask con- 
nected with a condenser. Carbon dioxide is evolved, as can be 
demonstrated by holding a test-tube containing lime-water at 
the outlet of the condenser so that the gas enters the tube. 
After an energetic evolution of gas has continued for some time, 
5 g. of erystallized oxalic acid are added, and the heating” re- 
newed. Formic acid distils (158). ry 

2. Decomposition of Mercuric Formate.—A portion of the 
distillate of 1 is agitated with a small quantity of finely-divided 
mercuric oxide, prepared by triturating the powder in a mortar 
with a little water. The resulting solution of mercuric for- 
mate is filtered from the excess of mercuric oxide, and heated. 
At first, carbon dioxide is evolved, and white mercurous formate 
precipitated. On further heating, the mercurous salt 1s decom- 
posed with evolution of carbon dioxide, and precipitation of 


metallic mercury: 


16 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


OOCH HCOO 
} He oocH-+ Hcooj fs = gen CO,+ HCOOH; 
~ Mercuric formate _ formate 


Hg|OOCH + H|COO|Hg =2He+ CO,-+ HCOOH. 


Mercurous formate 


The liquid now contains free formic acid, and, therefore, turns 
blue litmus red. It is filtered, and the filtrate is neutralized 
exactly with caustic soda or ammonium hydroxide; on addition 
of silver-nitrate solution, silver formate is precipitated. When 
this is heated, it decomposes with evolution of carbon dioxide, 
liberating half the formic acid and precipitating metallic silver, 
analogously to the mercury salt. The reaction of the liquid, 
therefore, again becomes acid. 

3. Action of Concentrated Sulphuric Acid on Formic Acid.— 
Another portion of the distillate of 1 is placed in a small flask, 
and kept cool during the slow addition of twice its volume of 
sulphuric acid. The flask is closed with a cork and delivery- 
tube, the end of the latter dipping under water in a pneumatic 
trough. On the application of heat, a gas is evolved. This is 
collected in a cylinder, and, on ignition, burns with the blue 
flame characteristic of carbon monoxide. Agitation of the 
contents of the cylinder with lime-water produces turbidity 
proving the formation of carbon dioxide by the combustion. 

4. Oxidation of Formic Acid by Potassium Permanganate.— 
The remainder of the formic acid obtained in 1 is heated with a 
small quantity of potassium permanganate and dilute sulphuric 
acid in the apparatus employed in 3, the end of the delivery-tube 
being immersed in lime-water contained in a test-tube. The 
permanganate solution is decolourized, and the carbon dioxide 
produced by the oxidation of the formie acid renders the lime- 
water turbid. 

5. Cacodyl Test for Acetic Acid.—On distilling sour beer 
(200 c.c.), an acid distillate is obtained with an odour of acetic 
acid. The distillate is nearly neutralized with a few drops of 


SATURATED ACIDS AND E.TERS. 17 


caustic-soda solution, a slightly acid reaction being maintained. 
It is then evaporated, the last traces of water being removed by 
heating over a free flame. A portion of the anhydrous sodium 
acetate thus obtained is mixed with arsenious oxide, and the 
mixture heated gently in a test-tube. The excessively dis- 
agreeable odour of cacodyl oxide, (CH,),As—O—As(CH,),, is 
soon perceived (80). This substance being extremely poisonous, 
great care must be exercised in carrying out the experiment, and 
the heating should be discontinued as soon as the odour has been 
detected. 

6. Stability of Acetic Acid towards Oxidizing-agents,—To 5 
drops of acetic acid are added small quantities of dilute potas- 
sium-permanganate solution and dilute sulphuric acid. Unlike 
formic acid, the acetic acid does not decolourize the permangan- 
ate solution. 

7. Silver Acetate.—1 g. of sodium acetate is dissolved in 
10 e.e. of water, and a solution of silver nitrate added. The 
precipitate of silver acetate, which is only slightly soluble in 
water at the ordinary temperature, is collected on a filter, and 
sufficient to saturate the aqueous solution at the boiling-point 
transferred to a beaker containing 50 e.e. of boiling, distilled 
water. On cooling, the salt crystallizes in long, silky needles. 
These are filtered off, spread on a porous plate to remove as 
much of the mother-liquor as possible, and dried in a dish on 
the water-bath. On carefully heating the salt in a porcelain 
crucible, it decomposes, leaving a residue of metallic silver. 

8. Test for Acetic Acid.—A few drops of ferric chloride are 
added to a dilute solution of sodium acetate. Owing to the for- 
mation of ferric acetate, the liquid turns blood-red. On boiling 
this solution, a reddish-brown, flocculent precipitate of basic 
acetate of iron is formed. If allowed to stand for a short time, 
this sinks to the bottom of the test-tube, leaving the super- 
natant liquid colourless. 

9. Oxidation of Ethyl Alcohol to Acetic Acid.—A mixture of 
6 g. of potassium dichromate and 10 g. of concentrated sulphuric 


18 4 LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


acid is introduced into a 100-c.c. distilling-flask connected with a 
condenser, and a solution of 2 e.e. of alcohol in 10 e.c. of water 
added drop by drop from a tap-funnel. On heating, acetic acid 
distils, and can be recognized by its odour, or, after careful 
neutralization with sodium -carbonate, by the ferrie-chloride 
test (8). 

Io. Saponification of Butter—About 5 g. of butter are 
saponified by boiling in a porcelain dish with 20 c.c. of a solu- 
tion of 1 part of caustic soda in 2 parts of water, the mixture 
being constantly stirred. After a few minutes, it begins to 
foam. The heating is continued for twenty minutes, and the 
contents of the dish allowed to cool. The liquid separates 
into two layers—the lower an aqueous solution of glycerol and 
caustic soda, and the upper the fused sodium salts of the 
fatty acids, which are insoluble in concentrated caustic-soda 
solution. When cold, the upper layer is semi-solid. It is sep- 
arated from the aqueous solution, and dissolved in water to 
separate it from unsaponified fat. This can be almost com- 
pletely removed by filtration through a moistened filter-paper. 

rr. Calcium and Lead Salts of the Higher Fatty Acids.—A 
part of the soap solution obtained by the method described in 10 
is neutralized with dilute acetic acid, and calcium chloride and 
lead acetate respectively added to separate portions. Pre- 
cipitates of the calcium and lead salts of the higher fatty acids 
are formed. 

12. Volatile Fatty Acids.—The rest of the soap solution is 
poured into a 100-e.e. distilling-flask connected with a condenser, 
and excess of dilute sulphuric acid added. On heating, water 
and the volatile jatty acids of the butter distil, chief of the latter 
being n-butyric acid. They can be detected by their odour 
and acid reaction. 

13. Higher Fatty Acids.—After the distillation of the vola- 
tile fatty acids, the residue in the flask consists of the solid 
higher fatty acids. It is transferred to a porcelain dish, allowed 
to cool, and the solid layer of fatty acids triturated with 


SATURATED ACIDS AND ESTERS. 19 


water several times to remove adhering sulphuric acid. To 
prove that the mixture has an acid reaction, it is dissolved in 
alcohol, and the solution added drop by drop to a very dilute 
solution of caustic soda, coloured red by a drop of phenol- 
phthalein. The colour disappears, and the acids dissolve, 
proving that the alkali has been neutralized. 

14. Soap.—A few drops of an alcoholic solution of phenol- 
phthalein are added to a concentrated, neutral soap solution. 
On dilution with a large-excess of water, the colourless liquid 
becomes red, owing to the liberation of free alkali by the hydro- 
lytic dissociation of the salts of the fatty acids (92). 

A solution of calcium sulphate is added to one of soap, 
whereupon the calcium salts of the higher fatty acids are pre- 
cipitated. 

15. Ethyl Acetate —Dry hydrochloric-acid gas is passed 
into a mixture of 10 e.c. of glacial acetic acid and 15 c.c. of ab- 
solute alcohol. The gas can be prepared by gently heating dried 
common salt with concentrated sulphuric acid in a flask, or can 
be obtained from a Kipp generator charged with fused ammo- 
nium chloride and concentrated sulphuric acid. The mixture 
is heated for an hour under a reflux-condenser, and then 
poured into water. Drops of ethyl acetate separate, a liquid 
characterized by its pleasant and refreshing odour. 

16. Velocity of Saponification of Ethyl Acetate—A small 
quantity of ethyl acetate is dissolved in water, and like 
volumes of the solution transferred to two test-tubes fitted 
with corks. One portion is agitated with a few drops of caustic 
potash or soda, and the other with a like volume of dilute sul- 
phurie acid. Since the saponification is effected much more 
rapidly by the caustic alkali than by the acid, the odour of the 
ester vanishes from the first tube much sooner than from the 
second. 

17. Solubility of Ethyl Acetate in Water.—An excess of 
ethyl acetate is vigorously agitated with 25 c.c. of water at 
the ordinary temperature till saturation is complete, and the 


20 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


aqueous solution is separated from the undissolved ester. 
When warmed, the solution becomes turbid from the separa- 
tion of ethyl acetate, which is more soluble in cold than in hot 
water. 


1 


X. ALDEHYDES AND KETONES. 
(106-121.) 
ALDEHYDES (106-118). 


1. Acetaldehyde.—A mixture of 60 g. of water, 20 g. of 
concentrated sulphuric acid, and 15 g. of ninety per cent. alco- 
hol is added to 13 g. of potassium dichromate contained in a 
200-c.c. fractionating-flask connected with a condenser. Some- 
times the oxidation begins spontaneously; should it not, how- 
ever, the flask is gently heated on a sand-bath, with a rapid 
current of cold water flowing through the condenser. A mix- 
ture of water, alcohol, acetaldehyde, and acetal distils, and can 
be used in carrying out the aldehyde-reactions described in 2, 
3, and 4. | 

2. Silver-mirror Test.—A small portion of the distillate is 
diluted with water in a clean test-tube, and a few drops of an 
ammoniacal silver solution added. This is prepared by adding 
a small excess of a solution of caustic soda to one of silver nitrate, 
and then ammonium hydroxide drop by drop in sufficient quan- 
tity to just redissolve the precipitate. After being shaken, 
the test-tube is immersed in water heated almost to its boiling- 
point. If the tube is thoroughly clean, the reduced silver is 
deposited on its sides as a mirror; if not, a black precipitate of 
the metal is obtained. 

3. Aldehyde-resin.—Caustic potash is added to another 
portion of the distillate, and the mixture warmed. A yellow 
colouration is produced at once, and, on further heating, a pre 
cipitate of aldehyde-resin 1 is formed. 


ALDEHYDES AND KETONES. 21 


4. SCHIFF’s Reaction.—Another portion of the distillate is 
added to a solution of magenta decolourized with sulphurous 
acid—ScuiFr’s reagent. The red colour of the dye is restored. 

5. a) Action of Formalin on Egg-albumin.—To 10 c.c. of a 
forty per cent. solution of formaldehyde—the ‘‘formalin” of 
commerce—is added 1 e.e. of the albumin of a hen’s egg. Coag- 
ulation at once takes place. 

b) Action of Formaldehyde on Gelatine.—T'o a solution of 
3 g. of gelatine in 100 c.c. of water are added 2 c.c. of 
“formalin.” An insoluble compound of gelatine and formal- 
dehyde is soon produced, causing coagulation of the liquid. 


KETONES (106-112, 119 and 120). 


6. Acetone.—About 50 g. of dried calcium acetate are 
heated to a high temperature in a retort connected with a con- 
denser. Acetone is the principal constituent of the distillate, to 
which the by-products present impart an empyreumatic odour. 
On addition of water, most of the liquid dissolves; the insoluble 
tar-like products are separated by filtration through a moistened 
filter-paper. 

7. Test for Acetone.—The filtrate obtained in 6 is added to a 
solution of mercuric nitrate made strongly alkaline by addition 
of alcoholic potash. On agitating the mixture, the acetone 
dissolves a part of the mercuric oxide suspended in the liquid. 
By repeated filtration, a clear filtrate is obtained. On addition 
of ammonium sulphide to this, a precipitate of mercuric sul- 
phide is formed, proving the presence of mercury in the solution. 

8. Addition-product of Acetone and Sodium Hydrogen Sul- 
phite.—5 c.c. of acetone are agitated with a like volume of a 
very concentrated solution of sodium hydrogen sulphite; a 
crystalline addition-product is precipitated, being almost insol- 
uble in the concentrated sulphite solution. On addition of 
water, it dissolves. 

9. Separation of Acetone from Aqueous Solution.—5 c.c. of 
acetone are added to a like volume of water, with which the 


\ 


22 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


ketone is miscible in all proportions. On addition of solid 
caustic potash to the mixture till saturation is complete, the 
liquid separates into two layers, the upper one being chiefly 
acetone, and the lower an aqueous solution of caustic potash 
containing traces of acetone. 

10. Oxidation of Acetone.—An aqueous solution of 2 e.e. cf 
acetone is prepared, and a dilute solution of potassium perman- 
ganate added till the pink colour of the liquid persists. After 
removal of the manganese dioxide by filtration, the filtrate is 
acidified with dilute sulphuric acid and distilled. After careful 
neutralization with sodium carbonate, the presence of acetic 
acid in the distillate can be proved by the ferric-chloride test 
(IX, 8). 


XI. UNSATURATED HYDROCARBONS. 
(122-134.) 


OLEFINES (122-129), 


1. Ethylene.—A mixture of 20 e.c. of alcohol of eighty per 
cent. strength and 120 c.c. of concentrated sulphuric acid is 
allowed to stand for some time, preferably for a fortnight or 
three weeks, in order that the formation of ethylsulphurie acid 
may be as complete as possible. It is then heated in a large 
flask on a sand-bath, the tendency to foam being checked by 
the introduction of sand into the flask. The ethylene evolved 
is collected over water in cylinders, being thereby freed from 
most of the carbon dioxide and sulphur dioxide generated along 
with it. 

2. Luminosity of the Ethylene Flame.—One of the cylinders 
is turned mouth upwards, and its contents ignited; the ethylene 
burns with a luminous flame. 

3. Action of Bromine on Ethylene.—A small quantity of 
bromine-water is added to another cylinder, the open end closed 


UNSATURATED HYDROCARBONS. a5 


with a glass plate, and the contents agitated. The red colour 
is discharged, and oily drops of ethylene bromide, C,H,Br,, 
collect on the sides of the cylinder, the characteristic odour of 
this compound also becoming perceptible. 

4. VON BAEYER'S Test for the Double Bond.—The gas in a 
third cylinder is shaken up with mixed aqueous solutions of 
potassium permanganate and sodium carbonate. The violet 
colour of the solution is discharged, and a brown precipitate of 
hydrated manganese dioxide, MnO,,nH,O, formed. 

5. Explosive Mixture of Ethylene and Oxygen.—A thick- 
walled cylinder one-quarter full of ethylene is filled up with 
oxygen, the contents mixed by shaking, and a light applied. 
The mixture explodes with a loud report. 

6. Unsaturated Hydrocarbons in Coal-gas.—Two cylinders 
are filled with coal-gas by displacement of water. By the ap- 
plication of the tests described in 3 and 4, the gas can be shown 
to contain unsaturated compounds. 

7. Double Linking in Amylene.—The presence of a double 
linking in amylene can be demonstrated by the reactions de- 
scribed in 3 and 4. 


ACETYLENE (132 and 133). 


8. Preparation of Acetylene.—A piece of calcium carbide 
is dropped into water contained in a 100-c.c. fractionating-flask 
fitted with a delivery-tube dipping under water, and the neck 
of the flask quickly closed with a cork. A vigorous evolution. 
of acetylene ensues. The gas is collected in cylinders, and sub- 
mitted to the tests described in 2, 3, and 4. 

g. Copper Acetylene and Silver Acetylene.—An ammoniacal 
solution of cuprous chloride is prepared by adding ammonium 
hydroxide to a mixture of cuprous chloride and water till solu- 
tion is complete. On addition of a portion of this liquid to a 
cylinder containing acetylene a red precipitate of copper acety- 
lene is formed, readily soluble in hydrochloric acid with evolu- 
tion of acetylene. 


24 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


An ammoniacal silver solution—prepared by adding ammo- 
nium hydroxide carefully to a solution of silver nitrate till the 
precipitate first formed has just redissolved—gives with acety- 
lene a white precipitate of silver acetylene. 


XII. MONOBASIC UNSATURATED ACIDS. 
(139-144. ) 


1. Double Bond in Almond Oil.—5 c.c. of almond oil, con- 
sisting principally of glyceryl oleate, are diluted with 10 c.c. 
of ether or carbon disulphide. A portion of the solution is agi- 
tated with bromine-water; the colour is discharged. To an- 
other portion is added a solution of potassium permanganate 
and sodium carbonate; a brown precipitate of hydrated man- 
ganese dioxide is obtained. 

2. Oleic Acid from Almond Oil.—5 c.c. of almond oil are 
saponified by the method described in IX, 10, the heating with 
caustic soda being continued for not less than an hour. Period- 
ically, water is added to replace that lost by evaporation, The 
resulting sodium-soap is dissolved in water, and the solution 
acidified with dilute sulphuric acid. The liberated oleic acid 
forms a liquid layer on the surface of the aqueous solution, from 
which it is removed by the aid of a separating-funnel. The 
tests for double linkings described in XI, 3 and 4, are carried out 
with portions of this acid. 

3. Elaidic Transformation.—Some of the liquid oleic acid is 
poured into 2 or 3 c.c. of a concentrated solution of sodium 
nitrite, a small quantity of dilute sulphuric acid added, and 
the mixture allowed to stand for some time. Owing to its trans- 
formation into elaïdie acid, the liquid oleic acid gradually be- 
comes solid. 

4. Fusion of Oleic Acid with Caustic Soda.—5 g. of solid 
caustic soda are heated to fusion with a few drops of water in an 
iron crucible, and 2 c.c. of oleic acid added. The mixture is 


CHLOROFORM AND IODOFORM. 25 


stirred, and maintained for some time in the fused state. After 
cooling, it is dissolved in water, and excess of dilute sulphuric 
acid added. On distillation from a fractionating-flask, an acid 
distillate is obtained, containing acetic acid. 

5. Lead Oleate.—A mixture of 5 c.c. of almond oil, 25 c.c. of 
water, and 10 g. of lead monoxide is boiled for not less than an 
hour in a porcelain dish, and constantly stirred. Water is 
added periodically to replace that lost by evaporation. After 
cooling, the water is poured off, and the plaster-like lead oleate 
(so-called “‘lead-plaster’”’) formed is triturated thoroughly with 
ether by the aid of a pestle. After filtering, and distilling the 
ether, the lead oleate is left in the semi-solid state. Addition of 
sulphuretted-hydrogen water proves the presence of lead, giv- 
ing a black precipitate of lead sulphide. 


XIII. CHLOROFORM AND IODOFORM. 
(150-152.) 


1. Preparation of Chloroform —25 g. of fresh bleaching- 
powder, 10 c.c. of alcohol of eighty-five per cent. strength, and 
10 e.e. of water are heated gently in a litre flask on a sand-bath 
till the reaction begins; the flame is then removed. ‘There is 
much foaming, and water and chloroform distil, the latter con- 
stituting the lower layer of the distillate. 

2. Action of Caustic Potash on Chloroform.—A few drops of 
chloroform are heated in a test-tube with a small quantity of 
dilute caustic potash, potassium chloride and potassium formate 
being produced. The mixture is neutralized so as to maintain 
a slightly alkaline reaction, and heated with a solution of mercuric 
chloride. Reduction to mercurous chloride, and then to metallic 
mercury, proves the presence of dissolved formate (IX, 2). 

3. Conversion of Chloroform into Potassium Cyanide.—1 c.c. 
of chloroform is heated in a test-tube for a short time with 5 c.c. 
of concentrated alcoholic ammonia and 1 e.e. of concentrated 


26 4 LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


alcoholic potash. The liquid is transferred to a porcelain dish, 
and evaporated to dryness on a water-bath. The presence of 
potassium cyanide in the residue is detected by the method 
employed in LASSAIGNE’s test for nitrogen (I, 3 a). 

4. Chloroform and Silver Nitrate.—1 c.c. of chloroform is 
agitated three or four times with water in a test-tube, using 
about 10 c.c. for each operation; this eliminates traces of hydro- 
chlorie acid, if present. More water and 2 or 3 drops of silver- 
nitrate solution are then added. A precipitate of silver chlo- 
ride is not formed. 

5. Iodoform Test for Alcohol.—To 1 c.c. of alcohol in a test- 
tube are added 10 c.c. of a moderately concentrated solution of 
iodine in potassium-iodide solution, and caustic-potash solution 
drop by drop till the brown colour of the iodine is discharged. 
A yellow, crystalline precipitate of iodoform.is obtained, dis- 
tinguished by its characteristic odour. Under the microscope, 
the crystals are seen to be six-sided plates. 


XIV. GLYCEROL. 
(157-160.) 


1. Preparation of Allyl Alcohol —10 c.c. of glycerol and 
12 g. of crystallized oxalic acid are heated in a retort connected 
with a condenser. At first, formic. acid distils (IX, 1), and 
soon oily streaks of allyl alcohol are seen on the sides of the 
retort. The distillation is continued with another receiver, this 
alcohol passing over. It is characterized by an irritating odour. 
On heating it with chromic-acid solution, the powerful, pene- 
trating odour of acrolein is perceived. 

2. Test for Glycerol.—t1 c.c. of glycerol is heated in a dish 
with 5 g. of sodium pyrosulphate, Na,S,O,; the odour of acro- 
lein is soon perceived. 

3. Action of Alkalis on Copper Salts in Presence of Glycerol — 
To 1 c.c. of glycerol are added 5 c.c. of dilute copper-sulphate 


SATURATED DIBASIC ACIDS. 27 


solution. On addition of caustic potash to this mixture, cop- 
per hydroxide, Cu(OH),, is not precipitated. Instead, a solu- 
ble copper alkoxide of glycerol is formed, imparting a deep-blue 
colour to the solution. 

4. BAUMANN and SCHOTTEN’s Test for Hydroxyl-groups.— 
A solution of 1 ¢.c. of glycerol in 2 ¢.c. of water is agitated with 
4 e.e. of benzoyl] chloride, until the odour of the chloride is no 
longer perceptible, caustic-potash solution being added slowly 
so as to maintain a slight alkaline reaction. The solid glyceryl 
tribenzoate formed is recrystallized from alcohol, the crystals 
dried between filter-paper, and their melting-point taken. 
M. P. 74°. 


XV. SATURATED DIBASIC ACIDS. 
(163-167.) 


OXALIC ACID (165). 


1. Preparation of Oxalic Acid from Wood.—A concentrated 
solution of caustic potash (not soda) is added to 10 g. of saw- 
dust, so as to form a thick paste. This is heated gently on a 
shallow iron dish, and constantly stirred. The first product 
is potassium formate; on further heating, this loses hydrogen, 
yielding potassium oxalate (2). The heating is continued for 
a few minutes after rapid evolution of hydrogen from the 
mass in large bubbles which burn on ignition has begun, and 
then stopped, to prevent decomposition of the oxalate formed. 
When cold, the reaction-mixture is lixiviated with water, fil- 
tered through a folded filter, and acidified with dilute acetic 
acid. On addition of caleium-chloride solution, calcium oxalate 
is precipitated, insoluble in acetic acid, but soluble in cold, and 
more readily in warm, hydrochloric acid. 

2. Conversion of Formates into Oxalates.—2 g. of dried 
sodium formate are heated to a high temperature in a test-tube 
closed with a cork and glass jet. Hydrogen is evolved, and can 


28 4A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


be ignited after all the air has been expelled from the tube. 
The white residue is proved to be sodium oxalate by dissolving 
it in water, and adding a solution of calcium chloride; a pre- 
cipitate of calcium oxalate, insoluble in dilute acetic acid, is 
formed. 

3. Calcium, Lead, and Copper Oxalates.—These are prepared 
by adding solutions of calcium chloride, lead acetate, and copper 
sulphate respectively to a ten per cent. solution of ammonium 
oxalate till precipitation is complete, 50 c.c. of the ammonium- 
oxalate solution being used for each experiment. The salts are 
collected on filters, washed thoroughly with water, and spread 
on porous plates to dry. The last traces of moisture are elimi- 
nated by heating them in porcelain dishes on the water-bath. 

4. Decomposition of Calcium Oxalate by Heat.—3 g. of cal- 
cium oxalate are heated in a hard-glass test-tube fitted with a 
delivery-tube When the temperature has risen above 200°, 
water of crystallization condenses on the sides of the tube; on 
further heating, carbon monoxide is evolved. The gas is col- 
lected in a cylinder, and its identity established by the method 
of IX, 3. The residue in the tube is calcium carbonate; when 
cold, it is treated with hydrochloric acid, causing a vigorous 
evolution of gas. This is proved to be carbon dioxide by its 
action on lime-water. 

5. Decomposition of Lead and Copper Oxalates by Heat.— 
The experiment described in 4 is carried out in separate tubes 
with 3 g. of lead oxalate and a like weight of copper oxalate. 
Both evolve carbon dioxide, as proved by the lime-water test; 
lead and copper remain in the tubes. 

6. Action of Concentrated Sulphuric Acid on Oxalic Acid.— 
A 100-c.c. distilling-flask 1s connected with a wash-bottle con- 
taining a mixture of caustic-potash solution and lime-water, 
and fitted with a delivery-tube. In the flask are placed 5 g. of 
oxalic acid and 10 c.c. of concentrated sulphuric acid. The 
flask is closed with a cork, and heated gently. Gas is evolved; 
partly carbon dioxide, which renders turbid the lime-water in 


SATURATED DIBASIC ACIDS. 29 


the wash-bottle; and partly carbon monoxide, which is not 
absorbed. The latter is collected in cylinders, and identified 
by the method of IX, 3. 

7. Complex Oxalates—a) A solution of ammonium oxa- 
late is added carefully to 2 c.c. of a five per cent. solution of 
copper sulphate. Copper oxalate is precipitated, and, on 
further addition of the ammonium salt, redissolves, forming 
copper ammonium oxalate. 

b) A solution of 2 g. of “salt of sorrel,’’ KHC,O,+ H,C,O, 
+2H,0O,in 10 c.c. of water is prepared. To this is added freshly- 
precipitated ferric hydroxide, obtained by adding ammonium 
hydroxide to a boiling, dilute solution of ferric chloride, allow- 
ing the precipitate to subside, and washing it by decantation. 
On warming, the ferric hydroxide dissolves, yielding potassium 
ferric oxalate, K,Fe(C,O,),. The green colour of this solution 
should be noted; it points to the absence of Fe-ions, and to the 
presence of complex [Fe(C,O,),|’’’-anions. 

c) A like solution of “salt of sorrel” is added to 5 e.e. of a 
ten per cent. solution of ferrous sulphate until the prccipitate 
first formed redissolves. The yellow colour of this solution is 
due to the complex [Fe(C,O,),|’’-anion. 

8. Dimethyl Oxalate.—Oxalic acid is dried at 100°, and 3 g. 
of the dry acid are dissolved in 10 c.e. of boiling methyl alcohol. 
On cooling, dimethyl oxalate crystallizes out. Some of the 
ester is dried by pressure between sheets of filter-paper, and its 
melting-point taken. M. P. 54°. 

9. Diethyl Oxalate.—A mixture of 7 g. of anhydrous oxalic 
acid and 10 e.e. of absolute alcohol is heated slowly in a 50-c.c. 
fractionating-flask connected with a condenser till the temper- 
ature rises to 110°. The distillate is then returned to the flask, 
and the heating continued till the thermometer reaches 180°. 
The fraction distilling between this temperature and 190° is 
collected separately, and is principally diethyl oxalate. 

10. Oxamide.—The esters obtained in experiments 8 and 9 
are dissolved separately in alcohol, and ammonium hydroxide 


30 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


added to each solution. From both a precipitate of oxamide is 
obtained, insoluble in water, alcohol, and ether. 


SUCCINIC ACID (167). 


rr. Barium Succinate.— Ammonium hydroxide is added to 
10 e.e. of a cold, saturated solution of succinic acid till neutrali- 
zation is complete. On addition of barium chloride, a white, 
crystalline precipitate of barium succinate is formed, the pre- 
cipitation being facilitated by addition of alcohol. 

12. Basic Ferric Succinate.—10 c.c. of a solution of succinic 
acid are carefully neutralized, and ferric chloride added. A 
brown, gelatinous precipitate of basic ferric succinate is formed. 

13. Succinimide.—A solution of 10 g. of succinic acid in 
ammonium hydroxide is evaporated in a porcelain dish on a 
sand-bath, and heated till the temperature of the fused mass is 
about 200°. The residue is transferred to a small fractionating- 
flask, and distilled as rapidly as possible. The distillate is 
succinimide, M. P. 125°. It can be crystallized from alcohol. 


XVI. HYDROXY-ACIDS OR ALCOHOL-ACIDS. 
(182-198.) 


LACTIC ACID ( 185), 


1. Decomposition of Lactic Acid by Dilute Sulphuric Acid.— 
5 c.c. of lactic acid are heated with a mixture of 5 c.c. of concen- 
trated sulphuric acid and 10 ¢.c. of water in a retort connected 
with a condenser. The distillate contains acetaldehyde and 
formic acid. These can be identified by the silver-mirror test 
(X, 2), and the mercuric-oxide test (IX, 2), respectively. 

2. Decomposition of Lactic Acid by Concentrated Sulphuric 
Acid.—A mixture of 5 c.c. of lactic acid and a like volume of 
concentrated sulphuric acid is heated in a retort fitted with a 
delivery-tube. The gas evolved by the decomposition of the 


HYDROXY-ACIDS OR ALCOHOL-ACIDS. 31 


formic acid first produced can be proved to be carbon monoxide 
by the method described in IX, 3. 

3. Test for Hydroxyl-groups with Phosphorus Pentachloride. 
_ —Ethy] lactate is prepared by distilling an intimate mixture of 
13 g. of potassium ethylsulphate and 10 g. of calcium lactate. 
The ester is dried by contact with granulated calcium chloride 
till no longer cloudy, and then poured over a small quantity 
of phosphorus pentachloride. This replaces its OH-group by 
Cl, evolving hydrochloric-acid gas, and forming «-chloropro- 
pionic acid. The mixture is poured into water, and the oil which 
sinks to the bottom agitated several times with small quantities 
of water, till this no longer gives a precipitate with silver nitrate. 
On applying BrIusTrIn’s test (I, 4 a) to the oil, a green coloura- 
tion is obtained, indicating the presence of chlorine. 


TARTARIC ACID (192-197). 


4. Potassium Tartrates.—Caustic potash is added drop by 
drop to 5 c.c. of a twenty per cent. solution of tartaric acid. A 
precipitate of potassium hydrogen tartrate is first formed, and, 
on further addition of caustic potash, redissolves, with produc- 
tion of the neutral tartrate. 

5. Iron Ammonium Tartrate.—A solution of 9 g. of ferrous 
sulphate is added to 15 c.c. of a solution of 1 part of tartaric 
acid in 2 parts of water; excess of ammonium hydroxide pro- 
duces no precipitate with this mixture. When agitated in pres- 
ence of air, this liquid absorbs oxygen, becoming lght-green, 
then dark-green, and finally brown. The absorption of oxygen 
can be demonstrated by carrying out the process in a flask 
closed with an air-tight cork; on immersion of the neck in water 
and removal of the cork, the water rises in the flask. After re- 
placement of the cork, the flask is withdrawn from the water, 
and an ignited wood-splint introduced into the residual gas; 
the flame is at once extinguished. 

6. FEHLING's Solution.—A solution of copper ee is 


32 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


added to one of tartaric acid, and then caustic potash in excess. 
The dark-blue liquid formed is known as FEHLING’s solution. 

7. Action of Heat on Tartaric Acid.—When heated in a test- 
tube, tartaric acid becomes brown, and acquires a caramel-like 
odour. 

8. Microchemical Method of Distinguishing between Tar- 
taric Acid and Racemic Acid.—a) Addition of calcium chlo- 
ride to a solution of tartaric acid saturated with ammonia gives 
a precipitate of calcium tartrate, somewhat soluble in acetic 
acid, and readily soluble in caustic potash and caustic soda. 

b) The last experiment is repeated with a solution of race- 
mic acid saturated with ammonia, and the crystals of caletum 
tartrate compared under the microscope with those of calcium 
racemate. 

9. Tartar Emetic.—A solution of potassium hydrogen tar- 
trate is prepared by dissolving 1 g. of tartaric acid in a small 
quantity of water, neutralizing with caustic potash, and adding 
a concentrated solution of a second gramme of tartaric acid. 
The precipitated potassium hydrogen tartrate is redissolved by 
heating, after addition of a little water. To this solution is 
added antimony oxide; it dissolves, forming tartar emetic. 


CITRIC ACID (198). 


10. Preparation from Lemons.—A small quantity of water is 
added to 10 e.e. of lemon-juice, the mixture filtered, and made 
alkaline with ammonium hydroxide. On addition of calcium 
chloride, no precipitate is formed; on boiling the mixture, 
tricalcium citrate is precipitated, and is redissolved as the 
liquid cools. 

rr. Action of Concentrated Sulphuric Acid on Citric Acid.— 
A solution of 5 g. of citric acid in cold, concentrated sulphuric 
acid is heated in a distilling-flask, fitted with a delivery-tube. 
The carbon monoxide evolved is identified by the method de- 
scribed in IX, 3 (248). 


CHLORAL HYDRATE. 33 


XVII. CHLORAL HYDRATE. 
(204.) 


1. Action of Water on Chloral.—3 g. of chloral hydrate are 
covered with concentrated sulphuric acid, and the mixture 
agitated. An oily layer of anhydrous chloral collects on the 
surface of the acid. This is separated from the sulphuric acid 
by the aid of a 50-c.c. tap-funnel, and brought into contact with 
a small quantity of water; heat is evolved, and solid chloral 
hydrate formed. 

2. Action of Caustic Potash on Chloral Hydrate.—A small 
quantity of caustic-potash solution is added to 1 g. of chloral 
hydrate dissolved in 10 e.e. of water. The odour of chloroform 
becomes perceptible, and the liquid is rendered turbid by the 
separation of minute drops of this substance. The presence of 
formic acid in the solution is proved by warming it, after careful 
neutralization and addition of a small quantity of mercuric 
chloride or silver nitrate (IX, 2). 

3. Silver-mirror Test for Chloral Hydrate.—A dilute solution 
of chloral hydrate is warmed in a test-tube on a water-bath with 
a small quantity of an ammoniacal solution of silver nitrate, 
prepared in accordance with the method described in X, 2. If 
the tube is clean, a silver mirror is deposited on its sides. 


XVIII. ALDEHYDE AND KETONE ALCOHOLS OR 
SUGARS. 


(206-231.) 


PROPERTIES OF THE MONOSES (207 and 208). 


1. Silver-mirror Test.—A ten per cent. solution of glucose is 
warmed in a clean test-tube in a water-bath with an ammoniacal 
solution of silver nitrate prepared as in X, 2. A silver mirror 
forms on the inner surface of the test-tube. 


34 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


2. Resinification with Caustic Alkalis.—A similar solution is 
boiled with a smafl amount of caustic-potash or caustic-soda 
solution. The liquid turns yellow, then brown, and finally 
resinifies. 

3. Reduction of FEHLING’s Solution.—On heating another 
portion of the glucose solution with FEHLING’s solution (XVI, 
6), reduction takes place, with formation of red cuprous oxide. 

4. Osazones.—A solution of phenylhydrazine in excess of 
dilute acetic acid is added to another portion of the glucose solu- 
tion in a test-tube. On warming the mixture in a water-bath, 
glucosazone precipitates in the form of microscopic, yellow 
needles. 


METHODS OF FORMATION OF THE MONOSES (210). 


5. Inversion of Sucrose (Cane-sugar).—A dilute solution of 
sucrose is boiled for several minutes with a few drops of dilute 
sulphuric acid. After this treatment, the solution answers to 
the glucose tests described in 1-4. 

6. Glycerose.—A mixture of 10 g. of glycerol and 20 c.c. of 
nitric acid of 1-18 specific gravity is heated in a beaker on the 
water-bath until oxides of nitrogen are evolved, and cooled 
quickly. After neutralization of the solution with caustic 
potash or soda, the presence of glycerose can be demonstrated 
by reactions 1-4. 


PENTOSES (211). 


7. Furfuraldehyde Test…— To 10 g. of bran contained in a 
half-litre flask is added a mixture of 5 g. of concentrated sul- 
phuric acid and 70 c.c. of water. The flask is connected with a 
condenser, and heated. The distillate contains furfuraldehyde 
(391), characterized by an agreeable odour. This aldehyde can 
be identified in two ways. 

a) On addition of a small quantity of aniline to the solu- 
tion, followed by concentrated hydrochloric acid, the liquid. 
acquires an intense red colour. 


ALDEHYDE AND KETONE ALCOHOLS OR SUGARS. ae 


b) A solution of phenylhydrazine in dilute acetic acid is 
added to the mixture containing furfuraldehyde, whereupon 
furfuraldehyde-hydrazone is precipitated in the form of an oil, 
which soon crystallizes. 


HEXOSES (212). 


8. Hydrochloric-acid Test.—A solution of a hexose is boiled 
with concentrated hydrochloric acid. The liquid becomes 
brown, and deposits “humus substances”; lsevulinie acid re- 
mains in solution (286). 


d-Glucose (212, 1). 


g. Calcium Alkoxide of d-Glucose— Milk of lime is added 
drop by drop to 10 e.e. of a solution of 1 part of d-glucose in 2 
parts of water, and the mixture agitated. The lime dissolves, 
forming the calcium alkoxide or saccharate of d-glucose. This 
is decomposed by carbon dioxide, with precipitation of calcium 
carbonate. 

ro. Glucosesulphuric Acid.—1 g. of d-glucose is triturated 
in a mortar with cold, concentrated sulphuric acid, added drop 
by drop till solution is complete. Glucosesulphuric acid is 
formed, and can be detected by diluting with water, adding 
barium carbonate till the mixture, thoroughly blended by the 
aid of the pestle, ceases to be acid, and filtering; the filtrate con- 
tains the barium salt of glucosesulphuric acid. Addition of 
dilute sulphuric acid decomposes the barium glucosesulphate, 
precipitating barium sulphate. 

11. Copper Alkoxide of d-Glucose.—A small quantity of a 
solution of 1 part of d-glucose in 2 parts of water is added to 2 ¢.c. 
of a ten per cent. solution of copper sulphate. On addition of 
caustic potash to the mixture, no precipitate is formed, the for- 
mation of a copper alkoxide of glucose imparting a dark-blue 
colour to the solution. 


36 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


12. Detection of d-Glucose in Urine.—Caustic-soda solution 
and a little bismuth nitrate are added to a five per cent. solution 
of d-glucose, and the mixture boiled. Black bismuthous oxide, 
BiO, is precipitated. 

13. Oxidation of d-Glucose by Nitric Acid.—A mixture of 1 g. 
of d-glucose and 10 c.c. of nitric acid of 1-3 specific gravity is 
evaporated to dryness on the water-bath. About 1 e.c. of 
water is added to the residue, and 5 e.c. of a concentrated solu- 
tion of potassium acetate. After a short time, potassium hydro- 
gen saccharate is precipitated. 


d-Fructose (212, 2). 


14. Alcoholic Character.—The alcoholic character of this 
compound can be demonstrated by the methods employed for 
d-glucose (9-11). 

15. Test for d-Fructose.—1 c.c. of a ten per cent. solution of 
d-fructose is heated with concentrated hydrochloric acid and 
some crystals of resorcinol. The liquid turns dark-red. 


d-Galactose (212, 6). 


16. Oxidation of d-Galactose to Mucic Acid.—A solution of 
1 g. of d-galactose is boiled for several minutes with nitric acid 
of 1-3 specific gravity, evaporated to small bulk, diluted with 
water, and cooled. Mucic acid separates as a crystalline powder, 
soluble with difficulty in cold water. If d-galactose cannot be 
obtained, lactose should be used instead (216). 

A small quantity of the mucic acid is washed with water to 
remove traces of nitric acid, dissolved in dilute caustic potash, 
and a drop of the solution allowed to evaporate to dryness on a 
microscope-slide. Under the microscope, the residue is seen to 
contain the characteristic, prismatic crystals of potassium 
mucate. 


ALDEHYDE AND KETONE ALCOHOLS OR SUGARS. 5 


HEXODIOSES (215-223). 


Sucrose (217-221). 


17. Properties Distinguishing Sucrose from the Monoses.— 
When heated with caustic alkalis, a ten per cent. solution of 
sucrose does not resinify; it does not reduce FEHLING’s solution; 
and, when warmed with a solution of phenylhydrazine in dilute 
acetic acid, gives no osazone (1-4). 

18. Action of Heat on Sucrose.—On heating a small quantity 
of sucrose in a test-tube, it turns brown, forming caramel, and 
evolving the characteristic odour of this substance. 

19. Tricaleium Saccharate.—10 c.c. of a twenty per cent. 
solution of sucrose are agitated with sufficient milk of lime to 
cause permanent turbidity, and filtered. When the filtrate is 
boiled, the nearly insoluble tricalcium saccharate, C,,H,.O,,-3CaO 
+ 3H,0, is precipitated. 

20. Inversion.—A solution of 2 g. of sucrose is inverted by 
boiling for several minutes with dilute sulphuric acid. After 
careful neutralization with caustic soda, the solution thus ob- 
tained has the properties characteristic of monoses, described in 


I-4. 
Lactose (216). 


21. Detection of Lactose in Milk.—A few drops of dilute 
acetic acid are added slowly to 25 c.c. of milk diluted with a 
like volume of water, the liquid being thoroughly mixed by 
stirring. The casein and fatty constituents of the milk are thus 
precipitated. The mixture is filtered through a folded filter. 
On warming part of the filtrate with Fruiina’s solution, the 
lactose causes reduction, with formation of red cuprous oxide. 
The rest of the filtrate is evaporated with dilute nitric acid to 
small bulk; d-galactose is formed by inversion, and oxidized to 
mucie acid, which can be recognized by the method of 16, 


38 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


22. Lactosazone.—On warming 5 c.c. of a ten per cent. 
solution of lactose with an acetic-acid solution of phenylhydra- 
zine, an osazone—lactosazone—is formed. 

23. “Sand-sugar.”— The taste of lactose is not so sweet as 
that of sucrose, and in the mouth it resembles sand, hence the 
name sand-sugar. 


POLYOSES (224-231). 
Starch (226 and 227). 


24. Starch-paste.—5 g. of powdered starch are washed with 
water on a filter-paper. The washed starch is transferred to a 
beaker containing 200 c.c. of boiling water, a faintly opalescent 
solution of starch-paste being obtained. 

25. Properties Distinguishing Starch from the Monoses.— 
If the starch has been washed with sufficient care, this starch- 
paste does not reduce FEHLING’s solution, and is not resinified 
by alkalis. 

26. Conversion of Starch into d-Glucose.—50 c.c. of the 
starch-paste solution are boiled with 10 c.c. of ten per cent. 
sulphuric acid for fifteen minutes. After neutralization with 
caustic soda, the liquid has the properties characteristic of 
monoses described in 1-4. 

27. Iodine Test for Starch.—A trace of an iodine solution is 
added to one of starch-paste, a deep-blue colouration being pro- 
duced. On heating, this disappears, but on cooling returns, 
provided the heating is not too prolonged. 

28. Barium Alkoxide of Starch.—A_ solution of barium 
hydroxide is added to a boiling solution of starch-paste. The 
barium alkoxide of starch is precipitated. 

29. Conversion of Starch into Dextrin.—A small quantity of 
starch is heated carefully in a test-tube, the residue agitated 
with cold water, and filtered. The filtrate contains dextrin, 
proved by the yellow colouration developed by heating with 


ALDEHYDE AND KETONE ALCOHOLS OR SUGARS. 39 


alkalis, and its precipitation from solution on addition of alco- 
hol. 

30. Potato-starch.—A small quantity of potato-starch is 
moistened with a few drops of water, a little of the mixture 
transferred to a microscope-slide, and examined under the 
microscope. The starch-granules are seen to have a charac- 
teristic shell-like appearance (226, Fig. 69). 


Cellulose (229-231). 


31. Hydrolysis of Cellulose.—A piece of filter-paper is dis- 
solved in cold, concentrated sulphuric acid by the method de- 
scribed in ro, the solution poured into water, and boiled for half 
an hour. When neutralized with caustic soda, it answers to 
the tests for monoses (1-4). 

32. Parchment-paper.—A strip of filter-paper. is immersed — 
in sulphuric acid containing half its volume of water, and at 
once transferred to a large quantity of cold water, and thor- 
oughly washed. This converts the cellulose into amyloid or 
parchment-paper, which gives a blue colouration with iodine. 
Although wet, the parchment-paper is very tough, and cannot 
be.torn readily. 

33. Solubility of Cellulose in SCHWEITZER’s Reagent.—An 
ammoniacal solution of copper oxide is prepared by adding 
freshly-precipitated, washed copper hydroxide to 10 c.c. of con- 
centrated ammonium hydroxide till no more dissolves. When 
placed in this, filter-paper (cellulose) dissolves. On addition 
of dilute hydrochloric acid to the solution, the colour is dis- 
charged, and an amorphous, flocculent precipitate of cellulose 
deposited. 

34. Nitrates of Cellulose.—A small piece of cotton-wool is 
immersed for several seconds in a cold mixture of one part of 
concentrated nitric acid and two parts of concentrated sul- 
phurie acid, nitrates of cellulose being formed. It is then 
washed carefully with much cold water, and dried at the ordi- 


40 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


nary temperature. A part held with tongs in a Bunsen flame 
burns energetically. Another portion is agitated with a mix- 
ture of alcohol and ether, and the liquid—a solution of collodion 
—poured on a glass plate; on evaporation of the solvent, a 
transparent skin is left. 

The remainder of the cellulose nitrates is moistened with a 
small quantity of ethyl acetate. A gelatinous mass is formed, 
which, when dry, burns slowly. In this form guncotton is 
employed in artillery, under the name ‘‘smokeless powder.” 

35. Detection of Lignin in Paper.—A sheet of paper is 
coated with a solution of aniline in hydrochloric acid. If made 
from wood, the paper acquires a yellow colour (230). 


XIX. HYDROCYANIC ACID, AND ITS SIMPLE AND 
COMPLEX SALTS. 


(242 and 243.) 


1. Hydrocyanic Acid.—10 c.c. of a cold, saturated solution 
of potassium ferrocyanide are poured into a distilling-flask con- 
nected with a condenser, and 20 c.c. of twenty per cent. sul- 
phuric acid added. The open end of the condenser is dipped 
into a test-tube containing water and a few drops of concen- 
trated caustic potash or soda. On heating, hydroeyanie acid 
distils, and is converted into potassium cyanide. 

2. Prussian-blue Test.—To part of the solution obtained in 
the last experiment is added a mixture of a ferrous salt and a 
ferric salt. On acidifying with hydrochloric acid, a precipitate 
of Prussian blue is formed (I, 3 a). 

3. Silver Cyanide.—A drop of a dilute solution of silver 
nitrate is added to 10 c.c. of a solution of 1 g. of potassium 
cyanide in 100 ¢.c. of water. On agitating the mixture, the 
precipitate first formed redissolves, yielding a double cyanide of 
potassium and silver, KAg(CN),. On further addition of silver 


HYDROCYANIC ACID, AND ITS SIMPLE AND COMPLEX SALTS. 41 


nitrate, a permanent precipitate of silver cyanide, AgCN, is 
obtained. 

4. Hydrolysis of Potassium Cyanide.—25 c.c. of the solution 
of potassium cyanide prepared for experiment 3 are boiled in a 
flask. The evolved ammonia turns a strip of red litmus-paper 
blue. 

5. Conversion of Ammonium Formate into Hydrocyanic Acid. 
—3 g. of ammonium formate are submitted to dry distillation in 
a small distilling-flask connected with a condenser dipping into 
a test-tube with very dilute caustic soda. The presence of 
hydrocyanic acid in the distillate can be demonstrated by the 
Prussian-blue test (2). 

6. Double Ferrocyanide of Potassium and Calcium.—A small 
quantity of a calcium-chloride solution is added to a cold, sat- 
urated solution of potassium ferrocyanide. The double ferro- 
cyanide, K,CaFe(CN),, is precipitated. 

7. Ferroeyanie Acid.—Concentrated hydrochloric acid is 
added to 5 c.c. of a strong solution of potassium ferrocyanide. 
White ferrocyanic acid, H,Fe(CN),, is precipitated. When 
collected on a filter-paper, it soon turns blue, Prussian blue 
being formed by decomposition and oxidation. 

„8. Action of Concentrated Sulphuric Acid on Potassium 
Ferrocyanide.—5 g. of potassium ferrocyanide are warmed with 
concentrated sulphuric acid in a fractionating-flask. The 
evolved carbon monoxide can be identified by the method 
described in IX, 3. 

g. Action of Heat on Potassium Ferrocyanide.—2 g. of potas- 
sium ferrocyanide are heated to redness in a crucible; when 
cold, the residue is lixiviated with water, and the mixture 
filtered quickly. The solution contains potassium cyanide, as 
can be proved by the Prussian-blue and silver-nitrate tests 
(2 and 3). 

10. Potassium Ferricyanide.—Bromine-water is added to 
a solution of potassium ferrocyanide, which converts it into 
potassium ferricyanide. This is proved by addition of ferric 


42 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


chloride, which produces a brown colouration, instead of a pre- 
cipitate of Prussian blue. 

11. Reduction of Potassium Ferricyanide.—Litharge, PbO, 
is added to a solution of potassium ferricyanide containing 
caustic potash. The solid beeomes brown, the lead monoxide 
being oxidized to lead dioxide, PbO,. After filtering, and add- 
ing ferric chloride to the filtrate, a precipitate of Prussian 
blue is formed, proving the presence of potassium ferrocyanide. 

12. Oxidation of Potassium Ferrocyanide by Potassium Per- 
manganate.—Sulphuric acid is added to a dilute solution of 
potassium ferrocyanide. This mixture decolourizes potassium 
permanganate, forming potassium ferricyanide, which gives a 
brown colouration with ferric chloride. 


XX. POTASSIUM CYANATE AND POTASSIUM 
THIOCYANATE. 


(244 and 245.) 


1. Potassium Cyanate.—Litharge, PbO, is added to 3 g. of 
fused potassium cyanide in a crucible so long as reduction to 
metallic lead is rapid. The potassium cyanate, KCNO, formed 
is extracted with water. On addition of sulphuric acid, carbon 
dioxide is evolved, since the liberated cyanic acid reacts at once 
with the water to form carbon dioxide and ammonia. The 
liquid in the flask is made alkaline with caustic soda, and heated. _ 
The evolved ammonia turns blue a strip of moist, red litmus- 
paper held in the mouth of the flask. 

2. Potassium Thiocyanate. —10 c.c. of potassium-cyanide 
solution are boiled for some minutes with “flowers of sulphur,” 
and filtered. Addition of ferric chloride to the filtrate gives a 
blood-red colouration, proving the formation of potassium 
thiocyanate. | 

3. Silver Thiocyanate— With silver nitrate a solution of 
potassium thiocyanate produces a white, cheese-like precipi- 


DERIVATIVES OF CARBONIC ACID. 43 


tate of silver thiocyanate, AgCNS, insoluble in dilute nitric 
acid. 


XXI DERIVATIVES OF CARBONIC ACID. 
(248-256.) 


CARBON DISULPHIDE (250). 


1. Inflammability—A few drops of carbon disulphide are 
poured into a porcelain basin, and ignited. The liquid burns 
with a blue flame, forming carbon dioxide and sulphur dioxide, 
the presence of the latter being made evident by its character- 
istic, suffocating odour. 

2. Volatility —On blowing upon a few drops of carbon 
disulphide in the palm of the hand, a sensation of cold is ex- 
perienced. 

3. Solvent Power.—Some linseed is crushed in a mortar, 
transferred to a test-tube, and covered with a small quantity 
of carbon disulphide. After about a minute, the liquid is 
poured on a clock-glass or watch-glass, and allowed to evaporate 
spontaneously. ‘The residue is linseed oil. ; 

4. Barium Trithiocarbonate.—5 g. of barium sulphide are 
boiled with water for a few seconds, and the mixture filtered. 
About 1 e.e. of carbon disulphide is added to the warm fil- 
trate, the mixture vigorously shaken, and allowed to cool. A 
yellow precipitate of barium trithiocarbonate is deposited. 

5. Potassium and Copper Salts of Xanthic Acid.—10 c.c. of a 
twenty per cent. solution of caustic potash in absolute alcohol 
is agitated with successive quantities of carbon disulphide, till 
potassium xanthate separates out. The precipitation of the 
salt is facilitated by addition of a small amount of ether. It 
is collected on a filter, dried between layers of filter-paper, and 
dissolved in water. On adding a solution of copper sulphate, a 
brownish-black precipitate of cupric xanthate is formed. This 
changes so quickly to yellow cuprous xanthate as to be hardly 
perceptible, 


44 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


UREA (252 and 253). 


6. WOHLER’s Synthesis.—Potassium cyanate, prepared by 
the method of XX, 1, is dissolved in water. Ammonium sul- 
phate is added, producing potassium sulphate and ammonium 
cyanate. The solution is evaporated almost to dryness on the 
water-bath, and the urea formed by the intramolecular re- 
arrangement of the ammonium cyanate extracted with alcohol. 
The solvent is distilled, leaving a residue of urea. 

7. Urea Oxalate.— The urea obtained in the last experiment 
is dissolved in a very small quantity of water, and a concen- 
trated solution of oxalic acid added. A crystalline precipitate 
of urea oxalate is deposited. 

8. Urea Nitrate from Urine.—About 10 c.c. of urine are 
evaporated to small bulk on a water-bath, and the residue 
allowed to cool. On addition of a few cubic centimetres of colour- 
less nitric acid of 1-4 specific gravity, a precipitate of urea 
nitrate is formed. The mother-liquor is poured off, and the nitrate 
purified by crystallization from a small quantity of hot water. 

9. KNoP’s Method for the Estimation of Urea in Urine.—A 
solution of bromine in cold caustic potash (German, Bromlauge) 
is added to 10 e.e. of urine contained in a distilling-flask fitted 
with a delivery-tube: The urea at once begins to decompose, 
evolving nitrogen. This is collected over water, and tested 
with a lighted taper. | 

10. BUNSEN’s Method for the Estimation of Urea in Urine. — 
10 c.c. of urine are heated with baryta-water in a flask. A 
strip of red litmus-paper held in the mouth of the flask is turned 
blue by the ammonia liberated. At the same time, the pre- 
cipitated barium carbonate renders the liquid turbid. 

11. LIEBIG’s Method for the Estimation of Urea in Urine.— 
A solution of mercuric nitrate is added to 10 c.c. of a two per 
cent. solution of urea. A white precipitate of the composition 
2CON,H,- Hg(NO.),-3Hg0 is formed. When excess of the 
mercuric nitrate has been added, a drop of the solution brought 


DERIVATIVES OF CARBONIC ACID. 45 


into contact with one of sodium carbonate gives a yellow pre- 
cipitate of basic nitrate of mercury. 

12. Action of Heat on Urea.—1 g. of urea is carefully heated 
in a test-tube; it melts, and evolves ammonia, which can be 
identified by means of a strip of red litmus-paper. The fusca 
mass soon re-solidifies, and the heating is stopped. The residue 
is lixiviated with a small quantity cf cold water, biuret going 
into solution. This substance can be identified by the biuret 
reaction. Caustic potash and one or two drops of a ten per 
cent. solution of copper sulphate are added to the liquid; the 
violet-red colouration produced is due to the formation of a 
copper compound of biuret. 

13. Cyanuric Acid.—This substance is the principal con- 
stituent of the residue in the test-tube after solution of the 
biuret in the last experiment. It is dissolved in warm water; 
after cooling, addition of copper sulphate and ammonium hy- 
droxide gives a crystalline, violet precipitate of copper ammo- 
nium cyanurate. 

CARBAMIC ACID (254). 


14. Calcium Carbamate— Ammonium hydroxide is added to 
10 c.c. of a ten per cent. solution of calcium chloride. On pass- 
ing carbon dioxide through the mixture, no precipitate 1s ob- 
tained, the calcium carbamate formed being soluble in water. 
When the solution is warmed, the carbamate decomposes, pre- 
cipitating calcium carbonate. 

15. Ammonium Dithiocarbamate——A drop of carbon disul- 
phide is added to a strong alcoholic solution of ammonia, and 
the mixture evaporated to dryness in a porcelain dish on a 
water-bath. Ammonium dithiocarbamate is formed first, but 
decomposes into ammonium thiocyanate and ammonium sul- 
phide. The latter volatilizes, and the presence of the former 
in the residue can be demonstrated by dissolving it in water, 
acidifying the solution with dilute hydrochloric acid, and adding 
ferric chloride. A blood-red colouration is obtained. caused by 
the formation of ferric thiocyanate (XX, 2). 


46 4A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


XXIL URIC ACID GROUP. 
(257 and 258.) 


1. Ammonium Urate.—A mixture of 50 c.c. of urine and 
2.5 e.e. of a concentrated solution of sodium carbonate is placed 
in a flask, and 5 c.c. of a saturated ammonium-chloride solution 
added. After a short interval, ammonium urate is precipitated, 

2. Di-potassium Urate——A small quantity of uric acid is 
agitated with water; it does not dissolve. On addition of 
dilute caustic potash, the readily soluble di-potassium salt is 
formed, and can be reconverted into uric acid by dilute acids. 

3. Murexide Test for Uric Acid.—A few cubic centimetres of 
nitric acid of 1-4 specific gravity are added to 0-5 g. of uric acid 
in a porcelain dish, and the mixture evaporated nearly to dry- 
ness on a water-bath. In addition to other products, alloxan- 
tine is formed. When treated with ammonium hydroxide, it 
forms a purple-red dye—murexide, the ammonium salt of pur- 
puric acid. 

4. Reduction of Silver Nitrate by Uric Acid.—A small quan- 
tity of uric acid is dissolved in a few drops of sodium-carbonate 
solution. When this is brought into contact with filter-paper 
moistened with a solution of silver nitrate, a black stain of 
metallic silver is formed, in consequence of the reducing action 
of the uric acid. 

5. Murexide Test for Caffeine—A few cubic centimetres of 
nitric acid of 1-4 specific gravity are added to 0-5 g. of caf- 
feine in a porcelain dish, and evaporated almost to dryness on a 
water-bath. A yellow stain of amalic acid, or tetramethyl- 
alloxantine, is left. On moistening this with ammonium hydrox- 
ide, it becomes purple. 


BENZENE AND ITS HOMOLOGUES. 4] 


XXIII. BENZENE AND ITS HOMOLOGUES. 
(263-270.) 


1. Stability of Benzene towards the Halogens.—On agitating 
a few cubic centimetres of benzene with bromine-water, the 
colour is not discharged. 

2. Absence of Double Bonds in Benzene.—Benzene is agi- 
tated with a solution of potassium permanganate and sodium 
carbonate—von BAEYER'’s reagent (123 and 263). The violet- 
red colour remains unaltered. 

3. Nitrobenzene.—2 c.c. of benzene are added drop by drop 
to a mixture of 4 c.c. of concentrated sulphuric acid and 2 c.c. 
of nitric acid of 1-5 specific gravity, the flask being cooled with 
running water to prevent rise of temperature. The benzene 
dissolves, and, on pouring the acid mixture into water, nitro- 
‘ benzene separates and sinks to the bottom. It has a char- 
acteristic odour, resembling that of oil of bitter almonds. 

4. Benzenemonosulphonic Acid.—5 c.c. of benzene are 
brought gradually into contact with 10 c.c. of fuming sulphuric 
acid. At first heat is developed, and the hydrocarbon dissolves 
quickly; to complete the reaction, the mixture must be warmed 
gently. It is then poured into twice its volume of water, com- 
mon salt added, and the liquid heated until hydrochloric-acid 
gas is evolved. On cooling, sodium benzenesulphonate sepa- 
rates in crystalline plates. 

5. FRIEDEL and CRAFTS’ Reaction.—1 g. of aluminium chlo- 
ride is added to 5 e.e. of benzene, and a small quantity of chloro- 
form dropped into the mixture. There is a vigorous evolution 
of hydrochloric-acid gas, and triphenylmethane is formed. 

6. Formation of Benzene from Calcium Benzoate.—10 g. of 
calcium benzoate are mixed with a like weight of soda-lime, 
and heated in a retort connected with a condenser, Benzene 


48 4 LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


distils, and can be identified by its odour, by the fact that it 
floats on water, and by converting it into nitrobenzene with a 
mixture of concentrated nitric and sulphuric acids in accord- 
ance with the method described in 3. 

7. Oxidation of Side-chains.—1 c.c. of toluene is heated 
with a solution of potassium permanganate and sodium car- 
bonate. The purple colour is discharged, and manganese diox- 
ide precipitated, in consequence of the oxidation of the side- 
chain. 


XXIV. MONOHALOGEN COMPOUNDS. 
(272 and 273.) 


1. Stability of Monochlorobenzene towards Alcoholic Potash 
or Soda.—5 c.c. of monochlorobenzene are heated with 10 c.c. 
of ten per cent. alcoholic potash or soda for a few minutes, and 
the liquid diluted with water. The monochlorobenzene is pre- 
cipitated unchanged as an oily liquid. To prove this, it is sep- 
arated by means of a tap-funnel, dried by contact with granu- 
lated calcium chloride for a few minutes, and its boiling-point 
determined by the method of III, 5. Monochlorobenzene boils 
at 132°. q 

After separation of the monochlorobenzene, the aqueous 
liquid is acidified with nitric acid, and silver nitrate added. It 
does not become turbid, proving that the caustic alkali has not 
reacted with the Cl-atoms of the monochlorobenzene. 

2. Saponification of Benzyl Chloride by Caustic Potash or 
Soda.—1 c.c. of benzyl chloride is warmed for a short time with 
10 c.c. of ten per cent. alcoholic potash or soda, and the mixture 
diluted with a large excess of water. If the heating has been 
of sufficient duration, no benzyl chloride separates. After acidi- 
fying with nitric acid, the solution gives with silver nitrate a 
heavy precipitate of silver chloride. 

3. Benzyl Iodide.—A small quantity of benzyl chloride is 
heated with an alcoholic solution of potassium iodide in a fume- 


MONOHYDRIC PHENOLS. 49 


cupboard. Benzyl iodide is formed, and gives off an extremely 
irritating odour, productive of tears. 


XXV. MONOHYDRIC PHENOLS. 
(274-276. ) 


1. Preparation of Phenol from Calcium Salicylate.—10 g. of 
calcium salicylate are heated in a retort connected with a con- 
denser. Phenol distils, and can be recognized by its odour, and 
by the reactions described in 4 and 5. 

2. Preparation of Phenol by Fusion of Sodium Benzenesul- 
phonate with Caustic Soda.—10 g. of sodium benzenesulphonate, 
3 g. of solid caustic soda, and a small quantity of water are 
heated in an iron dish to the temperature of fusion, the mixture 
being continually stirred. When cold, it is dissolved in water, 
the solution poured into a fractionating-flask, and dilute sul- 
phuric acid added slowly. Much sulphur dioxide is evolved, 
and can be recognized by its characteristic odour. The flask 
is connected with a condenser, and heated. Phenol distils along 
with water, and is identified by the methods of 4 and 5. 

3 Boarn Phenoxide.—1 g. of phenol is agitated with 
enough water to form an emulsion; on addition of caustic-soda 
solution, this dissolves, forming sodium phenoxide. When car- 
bon dioxide is passed through the liquid for a considerable 
time, phenol is liberated, and the mixture rendered turbid. 

4. Tribromophenol.—Bromine-water is added to a two per 
cent. aqueous solution of phenol. Tribromophenol is precipi- 
tated. 

5. Ferric-chloride Test for Phenol.—On addition of a drop of 
ferric-chloride solution to a one per cent. solution of phenol, an 
intense violet colouration is obtained. 

6. Depression of the Freezing-point of Phenol.—5 c.c. of 
phenol are melted in a test-tube by very careful heating over a 
tiny flame. After introduction of a thermometer, the liquid is 


50 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


allowed to cool. When crystals begin to form, the mercury 
ceases falling, and rises, the highest temperature indicated being 
the freezing-point. For anhydrous phenol, this is 39°. . 

The phenol is again melted, and 1 drop—about 0-05 g.—of 
water added. The freezing-point is determined as before, and 
found to be about 4° lower. 

7. Action of Nitric Acid on Phenol.—A cubic centimetre of 
phenol is added drop by drop to 10 ¢.c. of nitric acid of specific 
gravity 1-3, the liquid being continually agitated, and, finally, 
heated to boiling. On cooling, picric acid is precipitated. 
When recrystallized from water, it is obtained as yellow, needle- 
like crystals. 

8. Cresol.— With bromine-water and ferric chloride respec- 
tively, an aqueous solution of cresol gives reactions similar to 
those obtained with phenol (4 and 5). 


XXVI. MONOAMINO-COMPOUNDS AND THEIR 
DERIVATIVES. 


(282-291.) 


1. Aniline.—35 c.c. of hydrochloric acid of 1-19 specific 
gravity are poured into a flask containing 6 g. of nitrobenzene, 
and 18 g. of tin-powder added in successive small portions. To 
prevent its contents becoming overheated, the flask is shaken, 
and cooled with water. The nitrobenzene is reduced to aniline, 
this combining with the excess of hydrochloric acid to aniline 
hydrochloride. When all the nitrobenzene has dissolved, and 
its odour is no longer perceptible, the aniline is set free by caus- 
tic potash or soda, and the mixture distilled. The aniline vola- 
tilizes with the steam, rendering the distillate turbid. 

2. Neutral Reaction of Aniline.—A small quantity of aniline 
is agitated with water. The solution thus prepared neither 
imparts a colour to phenolphthalein, nor turns red litmus blue. 


MONOAMINO-COMPOUNDS AND THEIR DERIVATIVES. 51 


3. Aniline Salts.—On addition of an acid, the turbid liquid 
obtained in 1 becomes clear, a soluble aniline salt being formed. 
Caustic potash or soda reprecipitates the aniline as an oil. 

4. Tribromoaniline.— With an aqueous solution of aniline 
or of one of its salts, bromine-water gives a precipitate of tri- 
bromoaniline. 

5. Bleaching-powder Test for Aniline.—A few drops of ani- 
line are agitated with water, and the solution separated from 
undissolved amine by passing it through a moist filter. A small 
quantity of a clear solution of bleaching-powder gives a deep- 
violet colouration with the filtrate. 

6. Potassium-dichromate Test for Aniline.—2 or 3 drops of 
aniline are dissolved in dilute sulphuric acid. On addition of 
potassium-dichromate solution, a precipitate—green, blue, or 
black according to the concentration—is obtained. The black 
precipitate is called aniline-black. 

7. Acetanilide.—A mixture of 9 c.c. of aniline and a like 
volume of glacial acetic acid is boiled in a flask with a reflux- 
condenser for several hours. On cooling, crystals of acetanilide 
(“antifebrine”’) are deposited. When recrystallized from a small 
quantity of alcohol, these melt at 112°. 

8. Carbylamine Reaction.—Aniline can be proved to be a 
primary amine by the carbylamine reaction (VII, 2). 

9. Diphenylamine.—0-1 g. of diphenylamine is dissolved in 
a small quantity of alcohol, and the solution poured into water. 
The amine is now suspended in the water in a fine state of di- 
vision, and can be dissolved by addition of concentrated hydro- 
chloric acid drop by drop to the liquid. On dilution of this 
solution with water, the diphenylamine is reprecipitated, the 
hydrochloride undergoing hydrolytic dissociation. 

10. Nitrosodimethylaniline.—1-4 g. of sodium nitrite dis 
solved in water is added gradually to a well-cooled solution of 
2-4 g. of dimethylaniline in 12-5 g. of twenty per cent. hydro- 
chloric acid. Yellow nitrosodimethylaniline hydrochloride is 
precipitated. It is collected on a filter, washed with dilute 


52 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


hydrochloric acid, and purified by crystallization from hot 
water. The salt is triturated with water, caustic soda is added, 
and the green nitrosodimethylaniline liberated is dissolved in 
ether. On distilling the ether, the base is obtained in splendid, 
yellowish-green leaves. These are boiled with caustic soda, 
whereby dimethylamine is evolved, and the liquid becomes 
dark-red owing to the formation of sodium nitrosophenoxide. 
The dimethylamine can be identified by its characteristic odour, 
and its alkaline reaction to litmus. 

11. Azobenzene, Hydrazobenzene, and Benzidine Sulphate.— 
A mixture of 2 ¢.c. of nitrobenzene and 20 c.c. of twenty per 
cent. alcoholic potash is gently warmed, and small quantities of 
zine-dust added. In consequence of the formation of azoben- 
zene, the liquid develops a red colour. On addition of more 
zine-dust, the colour is discharged, and hydrazobenzene pro- 
duced. When the liquid is poured into a quantity of dilute 
sulphuric acid sufficient to make it strongly acid, nearly insolu-- 
ble benzidine sulphate is soon precipitated. 

12. Diphenylurea.—1 g. of urea and 3 g. of aniline are gently 
boiled in a test-tube for fifteen to thirty minutes, and poured 
into a dish. On cooling, diphenylurea crystallizes out, the mix- 
ture becoming solid. The excess of aniline is removed by treat- 
ment with dilute hydrochloric acid, the residue washed with 
water, and crystallized from alcohol. 


XXVII. BENZOIC ACID AND ITS DERIVATIVES. 
(296-298.) 


1. Benzonitrile and Benzoic Acid.—10 g. of sodium ben- 
zenesulphonate are mixed with a like weight of dried potassium 
ferrocyanide, and the mixture submitted to dry distillation in a 
retort connected with a condenser. Benzonitrile and a trace of 
phenylearbylamine distil. The isonitrile is decomposed by 
warming with two drops of concentrated hydrochloric acid. 


BENZOIC ACID AND ITS DERIVATIVES. 53 


About 20 c.c. of ten per cent. caustic potash are added, and the 
mixture is boiled in a flask with a reflux-condenser. Ammonia 
is evolved, as can be proved by red litmus-paper, while the oily 
layer of benzonitrile disappears. The flask is cooled, and con- 
centrated hydrochloric acid added slowly; a white, flocculent 
precipitate of benzoic acid is deposited. 

2. Benzoic Acid from Gum-benzoin.—5 g. of finely-pow- 
dered gum-benzoin are mixed with sand, and heated gently in a 
porcelain dish on a sand-bath for an hour, care being taken to 
avoid fusion. The dish is covêred with a hollow paper-cone, 
into which the benzoic acid sublimes. 

3. Volatility of Benzoic Acid with Steam.—1 g. of benzoic 
acid is heated with water in a fractionating-flask connected 
with a condenser. The acid volatilizes with the steam, as is 
proved by the odour and acid reaction of the distillate. 

4. Ethyl Benzoate.—1 g. of benzoic acid is warmed with 5 c.c. 
of absolute alcohol and a few drops of concentrated sulphuric 
acid. The ethyl benzoate formed is characterized by a pepper- 
mint-like odour. 

5. Benzanilide.—A few cubic centimetres of water are added 
to 1 c.c. of aniline, and then alternately small quantities of 
caustic potash and benzoyl chloride drop by drop. The mix- 
ture is agitated constantly, care being taken to maintain it alka- 
line. Finally, the alkaline liquid is agitated till the odour of 
benzoyl chloride is not perceptible. The white precipitate of 
benzanilide is collected on a filter, washed with water till this 
is no longer alkaline, and crystallized from alcohol. M. P. 
158°. 

6. Benzamide.—3 g. of ammonium carbonate are reduced to 
fine powder in a mortar, and benzoyl chloride added drop by 
drop, the mixture being stirred continuously with the pestle 
till the odour of benzoyl chloride is no longer perceptible. It is 
lixiviated with cold water to remove ammonium chloride and 
carbonate, and the residue dissolved in a small quantity of hot 
water. On cooling, benzamide crystallizes out. M. P. 128°. 


54 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


This substance is tested for by warming with dilute caustic 
potash. Ammonia is evolved, and addition of hydrochloric 
acid to the alkaline solution precipitates benzoic acid. 

7. Oxidation of Cinnamic Acid by Potassium Permanganate.— 
0-1 g. of cinnamic acid is agitated with water, and several 
drops of a one per cent. solution of potassium permanganate 
added. The colour of the solution is discharged, a precipitate 
of hydrated manganese dioxide formed, and the liquid acquires 
an odour of benzaldehyde. 


XXVIII. BENZALDEHYDE. 
(299.) 


1. Silver-mirror Test.—2 drops of benzaldehyde are added 


to an ammoniacal solution of silver nitrate, prepared as de- _ 


scribed in X, 2. Gentle heating in a water-bath produces a 
silver mirror. 

2. Benzaldehydephenylhydrazone.— A few drops of benz- 
aldehyde are added to a solution of phenylhydrazine in dilute 
acetic acid. Benzaldehydephenylhydrazone is precipitated, and 
by crystallization from alcohol is obtained in large, fine crystals, 
melting at 152°. 

3. Sulphite Compound of Benzaldehyde.— A cubic centi- 
metre of benzaldehyde is agitated with a very concentrated 
solution of sodium hydrogen sulphite. The crystalline sulphite 
compound is precipitated, and the odour of benzaldehyde ceases 
to be perceptible. On warming with water, the sulphite deriva- 
tive is decomposed, and the benzaldehyde liberated. 

4. Action of Alcoholic Potash on Benzaldehyde.—On mix- 
ing 1 c.c. of benzaldehyde with 5 c.c. of a ten per cent. solution 
of alcoholic potash, heat is developed, and the liquid solidifies 
owing to the precipitation of potassium benzoate. The crystals 
are collected on a filter, washed with a small quantity of alcohol, 


DIAZONIUM COMPOUNDS AND AZO-DYES. 55 


and dissolved in water. Addition of hydrochloric acid pre- 
cipitates benzoic acid. 

The alcoholic filtrate contains benzyl alcohol (277), which 
can be identified by evaporating the ethyl alcohol, and carefully 
adding concentrated sulphuric acid to the residue. The benzyl 
alcohol resinifies. 

5. Oxidation of Benzaldehyde by Potassium Permanganate.— 
A few drops of benzaldehyde are heated with an aqueous solu- 
tion of potassium permanganate. Manganese dioxide is pre- 
cipitated, the aldehyde being oxidized to benzoic acid, which 
remains dissolved as potassium benzoate. When the odour of 
benzaldehyde is no longer perceptible, two drops of alcohol are 
added to reduce the excess of potassium permanganate, and 
the colourless liquid filtered. On acidifying the filtrate, ben- 
zoic acid is precipitated. 


XXIX. DIAZONIUM COMPOUNDS AND AZO-DYES. 
(302-804, and 320-324.) 


1. Benzenediazonium Chloride-—9-3 g. of aniline are dis- 
solved in about 100 e.e. of hydrochloric acid containing 9-2 g. 
of HCl. To this solution, maintained between 5° and 10° by 
the introduction of ice, is added ‘very slowly a concentrated 
aqueous solution of 7-2 g. of commercial sodium nitrite, the 
liquid being stirred constantly. The solution of benzenedia- 
zonium chloride thus obtained is kept in a vessel surrounded by 
ice. and used for experiments 2 and 3. 

2 Replacement of the N.-Group in Benzenediazonium Chloride 
by Hydroxyl.—A small quantity of the solution of benzene- 
diazonium chloride is warmed in a fractionating-flask con- 
nected with a condenser. When the evolution of nitrogen 
has ceased. the solution is distilled. water and phenol passing 
over. The latter can be identified by its odour, and by reac- 
tions XXV, 4 and 5 


56 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


3. Diazoaminobenzene.—Aniline is mixed with ten times its 
volume of water, and cnough hydrochloric acid to give a clear 
solution. Addition of part of the solution of benzenediazonium 
chloride prepared in 1 and solid sodium acetate produces a yel- 
low or brown precipitate of diazoaminobenzene. 

4. Aminoazobenzene.—A small quantity of diazoaminoben- 
zene is warmed gently with about twice its volume of aniline 
and some solid aniline hydrochloride. Aminoazobenzene is 
formed. On addition of concentrated hydrochloric acid and 
solid salt, steel-blue needles of aminoazobenzene hydrochloride 
are obtained. 

5. Dyeing with -Aminoazobenzene.—An alcoholic solution of 
aminoazobenzene is diluted with water, and a few drops of 
dilute hydrochloric acid added. A woollen thread immersed 
in the liquid for a quarter of an hour is dyed yellow, and the 
colour eannot be removed by washing with water. 

6. Reduction of Aminoazobenzene.— A small quantity of 
aminoazobenzene hydrochloride is brought into contact with 
tin and hydrochloric acid. It is decolourized, yielding p- 
phenylenediamine and aniline. The mixture is made strongly 
alkaline with caustic soda, and distilled, using a condenser. 
The presence of aniline in the distillate can be proved by the 
bleaching-powder test (XXVI, 5). 

7. Oxidation of Phenylhydrazine by FEHLING's Solution (305). 
—A drop of phenylhydrazine on a watch-glass is mixed with 
a small quantity of concentrated hydrochloric acid. There 
results phenylhydrazine hydrochloride, nearly insoluble in 
dilute hydrochloric acid. After pouring-off the excess of hydro- 
chlorie acid. a small quantity of the salt is dissolved in water in 
a test-tube. and Frnrina’s solution (XVI, 6) added. Reduc- 
tion takes place at ordinary temperature, with formation of 
cuprous oxide, Cu,O. 


POLY-SUBSTITUTED DERIVATIVES. ai 


XXX. POLY-SUBSTITUTED DERIVATIVES CONTAINING 
SIMILAR SUBSTITUENTS. 


(310-331.) 


1. Pyrogallol—On carefully heating 5 g. of well-dried gallic 
acid in a retort, carbon dioxide—which can be identified by the 
lime-water test—is evolved, and pyrogallol sublimes. The lat- 
ter is dissolved in water, and the solution divided into three 
parts. 

‘When silver-nitrate solution is added to one, metallic silver 
is eg ee. 

Addition of a drop of ferric chloride to the sedan produces 
an intense bluish-black colouration. 

The third portion is transferred to a thick-walled test-tube, 
caustic potash added, the tube closed with a closely-fitting cork 
or rubber stopper, and the mixture vigorously agitated. The 
oxygen in the tube is absorbed, the pyrogallol-solution turning 
brown. On removing the stopper under water, the latter rises 
in the tube. 

2. Benzoquinone-—To a drop of aniline in a dish are added 
a small quantity of potassium-dichromate solution and a drop 
of concentrated sulphuric acid. The pungent odour of benzo- 
quinone is perceived. 

3. Tests for Catechol, Resorcinol, and Quinol.— With a 
drop of ferric chloride, aqueous solutions of catechol and resor- 
cinol give a green and a deep-violet colouration réspectively. 
With bromine-water, resorcinol yields a precipitate of tribromo- 
resorcinol. 

Solutions of catechol and resorcinol are made alkaline with 
caustic soda. ‘They acquire a dark colour immediately. 

Addition of ammonium hydroxide to a solution of quinol 
turns it red-brown. 

4. m-Dinitrobenzene.—1-5 c.c. of benzene are added drop 
by drop to a mixture of 5 c.c. of concentrated sulphuric acid 


58 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


and 5 e.e. of fuming nitric acid, the liquid being agitated thor- 
oughly during the process. The solution is heated for a few 
minutes, allowed to cool, and poured into water. m-Dinitro- 
benzene is precipitated, and is freed from a small percentage of 
the ortho-compound and traces of the para-compound by crys- 
tallization from alcohol. M. P. 90°. 

5. Test for Nitrous Acid with m-Phenylenediamine. — To 
10 c.c. of a dilute solution of m-phenylenediamine are added a 
drop of a solution of sodium nitrite, and a drop of dilute sul- 
phurie acid. The liquid becomes brown, Bismarck-brown 
being formed. 

6. Phthalic Anhydride.—O-1 g. of phthalic acid is heated 
in a dish, covered with a watch-glass, on a sand-bath. Long 
needles of phthalic anhydride sublime. 

7. Fluorescein.—Some crystals of phthalic anhydride and a 
like quantity of resorcinol are heated for a few minutes with 1 c.c. 
of concentrated sulphuric acid. To prevent the liquid becom- 
ing dark-coloured, the heating must not be too prolonged, or 
the temperature too high. On dissolving the mixture in 100 c.c. 
of water and adding caustic soda, a beautifully fluorescent, yel- 
lowish-green solution containing fluorescein is obtained. 

8. Phenolphthalein.—A mixture of like quantities of phthalic 
anhydride and phenol is warmed with concentrated sulphuric 
acid, phenolphthalein being formed. When this is added to a 
dilute solution of a caustic alkali, a red colouration is produced. 

g. Red Anion of Phenolphthalein.—A few milligrammes of 
phenolphthalein are dissolved in absolute alcohol containing a 
trace of calcium hydroxide in suspension; the liquid remains 
colourless. On dilution with water, the caletum compound of 
the phthalein is ionized, with production of a red colour. 


Pao 


POLY-SUBSTITUTED DERIVATIVES. 59 


XXXI. POLY-SUBSTITUTED DERIVATIVES CONTAINING 
TWO OR MORE DISSIMILAR SUBSTITUENTS. 


(332-351.) 


1. p-Diazobenzenesulphonic Acid, —1-7 g. of sulphanilic 
acid, NH,-C,H,-SO,OH (1:4), are dissolved by heating with 
25 c.c. of two per cent. caustic soda. A concentrated aqueous 
solution of 1 g. of sodium nitrite is added, and the mixture 
poured into excess of cold, dilute sulphuric acid. After an in- 
terval, p-diazobenzenesulphonic acid is precipitated as a sand- 
like, crystalline powder. 

2. Nitrophenols.—To 18 c.c. of nitric acid of 1-17 specific 
gravity are added slowly 3 c.c. of phenol, liquefied by addition 
of a small quantity of water. During the process, the mixture 
is cooled, and agitated vigorously. A heavy, black oil separates 
from the aqueous liquid. After washing with water in a small 
separating-funnel, the oil is distilled with steam (III, 2). o-Nitro- 
phenol distils, and can be identified by its odour, and by its 
yellow crystals melting at 44°. The residue in the flask con- 
tains p-nitrophenol. 

3. Picric Acid.—On carefully heating 0-1 g. of picric acid in 
a test-tube, the acid melts and sublimes; more rapid heating 
causes. explosive decomposition, leaving a residue of carbon, 
At the same time, an odour resembling that of nitrobenzene 
becomes perceptible. 

4. Potassium Picrate.—Caustic potash is added to an alco- 
holie solution of 0-5 g. of picric acid. Bright-yellow potassium 
picrate is precipitated, collected on a filter-paper, and dried by 
exposure to the air. The dry salt is exploded by percussion, 
and by heating on a platinum or porcelain crucible-lid. Only a 
very minute quantity of the salt must be used for this experiment. 

5. Taste of Picric Acid.—0-1 g. of picric acid is dissolved in 
water; the solution thus obtained has a very bitter taste. 


60 4 LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


6. Dyeing with Picrie Acid.—A woollen thread immersed 
in the liquid is soon dyed bright-yellow. 

7. Isopurpuric Acid.—An aqueous solution of non 
eyanide is added to one of picric acid. A purple colouration, 
due to the formation of the potassium salt of isopurpuric acid, is 
produced. 

8. Chlcropicrin—0-5 g. of picric acid is warmed carefully 
with a solution of bleaching-powder. The pungent odour of 
chloropicrin (151), CC1,NO,, becomes perceptible. 

g. Ionization of Picric Acid in Aqueous Solution, —On 
warming a small quantity of picric acid with petroleum-ether 
in a test-tube, a colourless solution is obtained, the acid not 
being ionized in this solvent. When, however, this colourless 
solution is agitated with a small quantity of water, the latter 
acquires the deep-yellow colour characteristic of the anion of 
picric acid. 

10. Salicylic Acid.—0-5 g. of salicylic acid is heated gently 
in a test-tube; it melts, and sublimes. On heating to a higher » 
temperature, it decomposes partly into carbon dioxide and 
phenol, the characteristic odour of the latter becoming per-_ 
ceptible. 

11. Action of Bromine-water on Salicylic Acid.—Bromine- 
water added to a saturated solution of salicylic acid gives a 
precipitate of the formula C,H,Br,-OBr. 

12. Identification of Salicylic Acid and Phenol. — Ferric 
chloride is added to alcoholic and aqueous solutions of salicylic 
acid and phenol respectively. Salicylic acid gives the violet 
colouration in both solvents, phenol only in water. 

13. Calcium Salicylate —0-5 g. of salicylic acid is added to a 
mixture of calcium-chloride solution and ammonium hydroxide. 
On heating, calcium salicylate, C,H,O,Ca+ H,O, is precipitated. 

14. Action of Tannin on Gelatine.—A solution of tannin is 
added to one of gelatine. The gelatine is precipitated. 

15. Test for Tannin.—A dilute solution of tannin is turned 
dark-violet by a drop of ferric chloride. A piece of oak-bark 


TERPENES AND CAMPHORS. 61 


or cinchona-bark, an unroasted coffee-bean, and part of a gall- 
nut are extracted with boiling water in different dishes. The 
presence of tannin in all these solutions can be proved by the 
ferric-chloride test. 

16, Action of Tannin on Quinine.—On addition of a solution 
of tannin to one of quinine hydrochloride, the alkaloid is pre- 
cipitated. 

17. Interaction of Albumin and Tannin.—10 c.c. of milk 
are freed from casein and fat by the method described in XVIII, 
21. The presence of albumin in the filtrate can be proved by 
adding tannin, an insoluble compound of albumin and tannin 
being precipitated. 

18. Hydrolysis of p-Nitraniline Hydrochloride.—0-5 g. of 
p-nitraniline is dissolved by gentle heating with as small a quan- 
tity of concentrated hydrochloric acid as is necessary to effect 
solution. On addition of water, the yellow nitraniline is repre- 
cipitated, owing to almost complete hydrolytic dissociation of 
the hydrochloride. 


Ld 


XXXII. TERPENES AND CAMPHORS. 
| (358-363.) 


1. Artificial Camphor.— American or German oil of turpen- 
tine is dried by calcium chloride, poured off, and distilled. Dry 
hydrochloric-acid gas, prepared by the method of IX, 15, is led 
into 10 c.c. of the dry turpentine, the flask being cooled by ice. 
After some time, transparent crystals of pinene hydrochloride 
or “artificial camphor,’ C,,H,,-HCl, are deposited. The 
mother-liquor is poured off, and the crystals dried by pressing 
between layers of filter-paper. In odour and appearance pinene 
hydrochloride resembles camphor. 

2. Volatility of Camphor with Steam.—A piece of camphor 
is placed in water in a fractionating-flask connected with a con- 
denser. On heating, the camphor passes over with the steam. 


62 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


3. Camphor and Water.—A piece of camphor thrown upon 
the surface of water acquires a rotatory motion, due to disparity 
of the vapour tension for the different crystal faces. 

4. Camphoric Acid.—2 g. of camphor are heated in a flask 
with dilute nitric acid for some minutes, and evaporated almost 
to dryness in a porcelain dish. The residue is diluted with 
water, made alkaline with caustic soda, and the undissolved 
portion filtered off. If the filtrate is not too dilute, hydro- 
chloric acid precipitates camphoric acid, 


XXXII. BENZENE-NUCLEI LINKED TOGETHER BY 
CARBON. 


(364-369. ) 


1. Rosolic Acid.—A mixture of 2 c.c. of phenol, 0-5 g. of 
oxalic acid, and 5 e.e. of concentrated sulphuric acid is heated 
in a test-tube. It acquires a red colour. On pouring the liquid 
into water, and making it alkaline with caustic potash, a dark-_ 
red solution is obtained, containing the potassium salt of rosolic 
acid. 

2. Magenta.—1 c.c. of aniline is heated in a test-tube with 
1 g. of p-toluidine and 0-5 g. of mercuric chloride, magenta 
being formed. On pouring the liquid into water containing 
a small quantity of hydrochloric acid, a deep-red solution is 
produced. 

3. Action of Concentrated Hydrochloric Acid on a Solution 
of Magenta.—Concentrated hydrochloric acid is added to part 
of the solution obtained in 2. The liquid becomes yellow, owing 
to the formation of the hydrochloride of the rosaniline base 
containing 3HC]. When this is poured into a large quantity of 
water, the red colour is restored. 

4. Colour-base.—Excess of ammonium hydroxide or caustic 
potash is added to another portion of the magenta solution. 
The colour-base is formed, and the liquid decolourized. 


CONDENSED BENZENE-NUCLEI. 63 


5. Leuco-base.—A third portion of the magenta solution is 
treated with zine and hydrochloric acid, without the application 
of heat. ‘The leuco-base is formed, and the colour discharged. 


XXXIV. CONDENSED BENZENE-NUCLEI. 
(370-385. ) 


1. Action of Heat on Naphthalene.—0-5 ¢. of naphthalene is 
heated in a test-tube. It melts, and sublimes readily. 

2. Naphthalene Picrate.—3 c.c. of a concentrated ether 
solution of picric acid are mixed with a like volume of a concen- 
trated solution of naphthalene in that solvent. A yellow, crys- 
talline precipitate of naphthalene picrate is produced. 

3. Naphthalenemonosulphonic Acids.—A mixture of 0-5 g. 
of naphthalene and 2 c.e. of concentrated sulphuric acid is 
heated in a test-tube for a few minutes, allowed to cool, and 
poured into water. On treatment with barium carbonate by 
the method of VI, 2, the presence of the dissolved sulphonic 
acids is proved. 

4. a-Nitronaphthalene.—1 g. of naphthalene is brought into 
contact with 5 e.e. of concentrated nitric acid, and the mixture 
poured into water. The precipitated yellow a-nitronaphtha- 
lene is crystallized from a small quantity of alcohol, being ob- 
tained in yellow needles, melting at 61°. 

5. Crude Naphthol.—0-5 g. of naphthol is agitated with 
water; only a small quantity dissolves. On addition of caustic 
potash or soda, a solution is obtained, from which carbon diox- 
ide reprecipitates the naphthol. 

6. Martius’ Yellow.—1 g. of «-naphthol is dissolved in 3 c.c. 
of concentrated sulphuric acid, and the solution poured into 
3 c.c. of concentrated nitric acid. When this mixture is diluted 
with water, dinitro-a-naphthol is precipitated. It is filtered 
off, washed, transferred to a vessel containing water, and dis- 
solved by addition of a small quantity of caustic soda, with 


64 A LABORATORY MANUAL OF ORGANIG CHEMISTRY. 


formation of the sodium salt, Martius’ yellow. A woollen 
thread dipped into this solution becomes dyed deep-yellow. 

7. Naphthylamines.—0-5 g. of a-naphthylamine is dis- 
solved in dilute hydrochloric acid. With ferrie chloride this 
solution gives a blue precipitate. A similar solution of pure 
B-naphthylamine does not react thus. 

8. Congo-red.—A few centigrammes of congo-red are placed 
in water, and a drop of concentrated hydrochloric acid added. 
The liberated acid turns the liquid blue; addition of an alkali 
restores the red colour. 

9. Naphthionic Acid.—A mixture of 1 g. of a-naphthyla- 
mine and 3 c.c. of concentrated sulphuric acid is heated in a 
test-tube for a few minutes, and poured into water. On mak- 
ing the liquid alkaline with caustic soda, it exhibits an intense 
reddish-blue fluorescence, resulting from the formation of sodium 
naphthionate. 

ro. Oxidation of Anthracene by Chromic Acid. — Small 
quantities of an acetic-acid solution of chromic acid are added 
to a solution of 3 g. of anthracene in this solvent, until the ener- 
getic reaction has ceased. The liquid is poured into water, and 
the precipitated anthraquinone collected on a filter. 

ir. Test for Anthraquinone.—A few centigrammes of an- 
thraquinone are heated in a test-tube with zine-dust and caus- 
tic soda, a deep blood-red solution of oxanthranol being formed. 
On agitating this solution with air, the colour is discharged. 

12. Alizarin.—3 g. of anthraquinone are dissolved in 10 c.c. 
of fuming sulphuric acid, and the solution heated till a drop 
gives no turbidity with water. After cooling, the solution of 
anthraquinonesulphonic acid is poured into 100 c¢.c. of water, 
and neutralized by addition of solid sodium carbonate. The 
precipitated sodium sulphonate is collected on a filter, dried on 
a porous plate, and carefully heated to fusion on an iron dish 
with caustic potash and a small quantity of potassium chlorate. 
When cold, the product is dissolved in water, the solution being 


HETEROCYCLIC COMPOUNDS. 65 


coloured violet-red by the potassium salt of alizarin. Dilute 
sulphuric acid precipitates red alizarin. 


XXXV. HETEROCYCLIC COMPOUNDS. 
(386-394. ) 


1. Pyridine.-—Some drops of pyridine are added to a few 
cubic centimetres of water, the base dissolving completely. 
The solution has an alkaline reaction. 

2. Action of Pyridine on Ferric Chloride. — The aqueous 
solution of pyridine gives with one of ferric chloride a precipi- 
tate of ferric hydroxide. 

3. Action of Pyridine on Mercuric Chloride.—-A solution of 
mercuric chloride added to a pyridine solution precipitates a 
white, crystalline compound of pyridine and mercuric chloride. 

4. Test for Pyridine —Hydrochloroplatinic acid, H‚PtCl, is 
added to a small quantity of a solution of pyridine; no precipi- 
tate is formed. On boiling the mixture for a short time, a yel- 
low powder of the formula PtCl,(C;H;N), is deposited. This is a 
characteristic test for pyridine. 

5. Action of the Alkaloid-reagents on Pyridine.—The alka- 
loid-reagents (401)—among them tannin, phosphomolybdic 
acid, and picric acid—precipitate pyridine from solution. 

6. Stability of Pyridine towards VON BAEYERS Reagent.—A 
solution of potassium permanganate and sodium carbonate is 
added to one of pyridine. The violet-red colour is not altered. 

7. Stability of Pyridine towards Oxidizing-agents. — A solu- 
tion of pyridine is heated with sodium or potassium dichromate 
and concentrated sulphuric acid. The colour of the solution 
undergoes no change. 

8. Pyrrole-red.i—Water is added to a small quantity of 
‘“Dippel’s oil” (886) in a test-tube. and the mixture boiled. 
A wood-splint moistened with concentrated hydrochloric acid 
becomes coloured red by the vapour, pyrrole-red being formed. 


66 A LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


g. Indophenin Reaction.—A cubic centimetre of crude ben- 
zene and a like volume of concentrated sulphuric acid are 
brought into contact with a fragment of isatin. In presence of 
thiophen, a blue colouration is produced. 

10 c.c. of crude benzene are agitated repeatedly with warm, 
concentrated sulphuric acid, about 2 e.e. being used for each 
operation. The benzene is separated, and tested by the indo- 
phenin reaction. Either the blue colouration is not produced, 
or it is much less pronounced than in the first experiment. 

10. Tests for Antipyrine.—A solution of antipyrine is turned 
red by ferric chloride, bluish-green by potassium or sodium 
nitrite and acetic acid. 


XXXVI. CONDENSATION-PRODUCTS OF BENZENE AND 
HETEROCYCLIC NUCLEI. 


(395-399. ) 


1. SKRAUP’s Synthesis of Quinoline-—A mixture of 4 c.c. of 
aniline, 12 c.c. of glycerol, 2-5 ¢.c. of nitrobenzene, and 6 c.c. of 
sulphuric acid is heated carefully in a flask till the reaction 
begins, the burner being then removed. When it has moder- 
ated, the heating is resumed, and continued for five or ten min- 
utes. The liquid is cooled, poured into water, and distilled 
with steam (III, 2) after addition of excess of caustic soda. 
The turbidity of the distillate is caused by the presence of 
minute drops of quinoline. The characteristic odour of the 
base is perceived. 

2. Quinoline Hydrochloride——On addition of hydrochloric 
acid to the distillate obtained in 1. the liquid becomes clear, sol- 
uble quinoline hydrochloride being formed. Caustic soda or 
potash reprecipitates the quinoline in oily drops. 

3. Quinoline Picrate.—With a solution of quinoline hydro- 
chloride, a saturated, aqueous solution of picric acid gives a 
yellow, amorphous precipitate of quinoline picrate. 


ALKALOIDS. 67 


4. Qtinoline Dichromate.—With quinoline salts, potassium 
dichromate gives a yellow, crystalline precipitate of quinoline 
dichromate, (C,H,N),H,Cr,O,. 

5. Volatility of Indigo.—On heating 0-1 g. of indigo in a 
test-tube, a violet vapour is obtained. 

6. Solubility of Indigo in Nitrobenzene.—0-1 g. of indigo 
is heated with a small quantity of nitrobenzene. It dissolves, 
and, on cooling, crystallizes. 

7. Indigosulphonic Acid.—0-1 g. of indigo is dissolved in 
1 c.c. of fuming sulphuric acid. Indigosulphonie acid is formed, 
so that the indigo is not reprecipitated when the solution is 
poured into water. 

8. Oxidation of Indigo to Isatin——The solution of indigo- 
sulphonic acid obtained in 7 is warmed with a small quantity of 
concentrated nitric acid. It is decolourized, and isatin formed. 

g. “Indigo-vatting.’’—0-1 g. of powdered indigo is heated 
with a solution of sodium hyposulphite, Na,S,O, (“Inorganic 
Chemistry,” 83). Sodium thiosulphate, miscalled “sodium 
hyposulphite,’ must not be used. A strip of linen or cotton is 
immersed in the solution of indigo-white, and hung up to dry. 
The oxygen of the atmosphere oxidizes the indigo-white to 
indigo-blue. 


XXXVII ALKALOIDS. 
(400-411. ) 


1. Alkaloid-reagents.—A solution of an alkaloid, such as 
quinine hydrochloride or sulphate, is tested with solutions of 
the ordinary alkaloid-reagents; for example, tannin, phospho- 
molybdie acid, mercuric potassium iodide, and a solution of 
iodine in one of potassium iodide. With each a precipitate is 
formed. 

2. Nicotine.—10 g. of tobacco are boiled with 100 e.c. of 
water containing a small quantity of sulphuric acid. After 


68 4 LABORATORY MANUAL OF ORGANIC CHEMISTRY. 


filtering, the filtrate is rendered alkaline, and distilled. The 
distillate contains nicotine, and yields precipitates with plati- 
num chloride, mercuric chloride, and a potassium-iodide solu- 
tion of iodine. 

3. Fluorescence of Quinine-sulphate Solution.—0O-1 g. of 
quinine sulphate is dissolved in water containing sulphuric acid. 
The solution exhibits a blue florescence. 

4. Action of Chlorine on Quinine Salts.—Chlorine-water is 
added to a solution of a quinine salt until the liquid smells 
strongly of the gas. On addition of ammonium hydroxide, an 
emerald-green colouration is produced. 

5. Test for Strychnine.—A crystal of strychnine nitrate is 
placed in a porcelain dish, and a few drops of concentrated sul- 
phuric acid added. A small crystal of potassium dichromate 
produces with this liquid a very intense bluish-violet colour. 

6. Test for Brucine.—A small quantity of brucine yields a 
red colouration with concentrated nitric acid; on the applica- 
tion of gentle heat, this changes to yellow. Dilution with water, 
and addition of ammonium sulphide, renders the yellow solution 
violet. 


XXXVIII. ALBUMINS. 
(412-418.) 


1. Detection of Nitrogen and Sulphur in the Albumins.— 
A few cubic centimetres of a solution of albumin—prepared by 
dissolving white-of-egg in five times its volume of water—is 
heated with caustic potash. Ammonia is evolved, and can be 
detected by the aid of a moist strip of red litmus-paper. 

The liquid is diluted with water, and lead acetate added. 
The potassium sulphide formed in the last experiment reacts 
with the lead salt, precipitating black lead sulphide. 

2. “Salting-out” Albumin with Ammonium Sulphate. — 
Solid ammonium sulphate is added to 20 ¢.c. of the albumin 
solution. The albumin is precipitated. 


ALBUMINS. 69 


3. Coagulation of Albumin by Alcohol.—Strong alcohol 
added to a solution of albumin gives a precipitate of coagulated 
albumin. A similar precipitate is formed when an aqueous 
solution of albumin is boiled. Coagulated albumin is soluble 
in dilute caustic potash, in concentrated hydrochloric acid, 
and concentrated sulphuric acid. 

4. Coagulation of Albumin by Nitric Acid.—Dilute nitric 
acid is added to an albumin solution prepared by the method 
of 1. The albumin is precipitated. 

5. Biuret Reaction —A few drops of copper-sulphate solu- 
tion are added to 5 c.c. of a solution of albumin. Careful addi- 
tion of dilute caustic potash to the mixture precipitates copper 
albuminate. Excess of caustic potash redissolves the precipi- 
tate, producing a violet-red colouration. 

6. MILLON’s Reagent.—On boiling an albumin solution with 
MILLon’s reagent—a solution of mercuric nitrate containing 
nitrous acid—a red, coagulated mass is obtained. 

7. Xanthoprotein Reaction.—An albumin solution warmed 
with dilute nitric acid is coagulated, with production of a yellow 
colouration. 

8. ADAMKIEWICZ’s Reaction.—With concentrated sulphuric 
acid a solution of albumin in glacial acetic acid yields a violet 
colouration, due to the presence in the mixture of a small pro- 
portion of glyoxylic acid. 

9. Decomposition-products of Ceratin.—A feather is heated 
with concentrated caustic potash. It dissolves. and the solution 
thus obtained gives the reactions for nitrogen and sulphur, 
described in 1. 





# 








INDEX. 


The principal references are in old-style figures. 


A, 
Acetal, 20. 
Acetaldehyde, 20, 21. 
Acetamide, 2, 12. 
Acetanilide, 51. 
Acetate, Basic ferric, 17. 
Calcium, 21. 
Ethyl, 19, 20, 40. 
Ferric, 17. 
Lead, 4, 5, 18, 28, 68. 
Potassium, 36. 
Silver, 17. 
Sodium, 7, 17, 56. 
Acetic acid, 10, 16-18, 19, 22, 
27, ye 51. 
Test for, 17, 22. 
Acetone, 21, 22. 
Test for, 21. 
Acetylene, 23, 24. 
Copper, 23. 
_ Silver, 23. 
Acid, Acetic, 10, 16-18, 19, 22, 25, 
27, 37, 51 
Amalic, 46. 
Anthraquinonesulphonie, 64. 
Benzenemonosulphonie, 47. 
Benzoic, 53, 54, 55. 
n-Butyric, 18. 
Camphoric, 62. 
Carbamic, 45. 
Carbolic. See phenol. 
a-Chloropropionic, 31. 
Cinnamic, 54. 
Citric, 32. 
Cyanie, 42. 
Cyanuric, 45. 
p-Diazobenzenesulphonic, 59. 
Ethylsulphurie, 10, 11. 


Acid, Ferrocyanie, 41. 
Formic, 15, 16,17, 26, 30,3133) 
Gallic, 57. 
Glucosesulphuric, 35. 
Glyoxylie, 69. 
Hydroeyanie, 40, 41. 
Indigosulphonie, 67. 
Isopurpuric, 60. 
Lactic, 30, 31. 
Levulinic, 35. 
Methylnitrolic, 14. 
Mucic, 36, 37. 
Naphthionie, 64. 
Oleic, 24. 
Oxalic, 7, 15, 26, 27-29, 44, 62. 
Phthalic, 58. 
Picric, 50, 59, 60, 63, 65-67. 
Propionic, 15. 
Racemic, 32. 
Rosolic, 62. 
Salicylic, 6, 60. 
Succinic, 30. 
Sulphanilic, 59. 
Tartarie jo liio2. 
Uric, 46. 
Xanthic, 43. 
Acids, Alcohol-. 
droxy-. 
CnH.n0,, Saturated, 15-20. 
Higher fatty, 18, 19. 
Hydroxy-, 30-32. 
Monobasic unsaturated, 24, 25. 
Naphthalenemonosulphonic, 63. 
Saturated dibasic, 27-30. 
Volatile fatty, 18. 
Acrolein, 26. 
ADAMKIEWICz’s reaction, 69. 
Albumin, 2, 3, 21, 61, 68, 69. 


71 


See acids, hy- 


72 


Albuminate, Copper, 69. 
Alcohol-acids. See acids, hydroxy-. 
Alcohol, Allyl, 26. 
Benzyl, 55. 
Ethyl, 5, 9, ro, 11, 12, 17-20, 22, 
25, 26, 29, 43, 53, 69. 
Methyl, 29. 
Test for ethyl, 26. 
water in, 9, 10. 

Alcohols, Aldehyde-. 
Cn Hon, OH, 9, 10. 
Ketone-. See sugars. 

Aldehyde-alcohols. See sugars. 
-resin, 20. 

Aldehydes, 20, 21. 

Alizarin, 64, 65. 

Alkaloid-reagents, 65, 67. 

Alkaloids, 67, 68. 

Alkyl halides, 10. 

Allotropie modifications of carbon, 

4, 5. 

Alloxantine, 46. 

Allyl alcohol, 26. 

Almond oil, 24, 25. 

Amalie acid, 46. 

Amines, 12-14, 50-52. 

Test for primary, 12. 

Aminoazobenzene, 56. 
hydrochloride, 56. 

Ammonium copper cyanurate, 45. 
cyanate, 44. 
dithiocarbamate, 45. 
formate, 41. 
oxalate, 28. 
purpurate, 46. 
thiocyanate, 3, 45. 
urate, 46. 

Amylene, 23. 

Amyloid, 39. 

Analysis of carbon 

Qualitative, 1-4. 

Aniline, 34, 40, 50, 51, 52, 53, 55- 

57, 66. 


See sugars. 


compounds, 


-black, 51. 
hydrochloride, 56. 
Anthracene, 64. 
Anthraquinone, 64. 
-sulphonate, Sodium, 64. 
-sulphonic acid, 64. 
Antifebrine. See acetanilide. 
Antipyrine, 66. 
ania camphor, 61. 


ee _ 


INDEX. 


Azobenzene, 52. 


B. 


BaAEYer’s test for the double bond, 
VON, 23, 24, 47, 65. 

Barium alkoxide of starch, 38. 
ethylsulphate, 11. 
glucosesulphate, 35. 
succinate, 30. 
trithiocarbonate, 43. 

BAUMANN and SCHOTTEN’s test for 

hydroxyl-groups, 27. 

BEILSTEIN’S test, 2, 3, 10, 31. 

Benzaldehyde, 54, 55. 
-phenylhydrazone, 54. 

Benzamide, 53. 

Benzanilide, 53. 

Benzene, 7, 47, 48, 57, 66. 
-diazonium chloride, 55, 56. 
-monosulphonie acid, 47. 
=sulphonate, Sodium, 47, 49, 52. 

Benzidine sulphate, 52. 

Benzoate, Calcium, 47. 

Ethyl, 53. 
Potassium, 54, 55. 

Benzoic acid, 53, 54, 55. 

Benzonitrile, 52, 53. 

Benzoquinone, 57. 

Benzoyl chloride, 27, 53. 

Benzyl! alcohol, 55. 
chloride, 48. 
iodide, 48, 49. 

Bismarck-brown, 58. 

Biuret, 45. 
reaction, 45, 69. 

Boiling-point, Determination of, 7. 

Bone-charcoal, 4, 5. 

Bran, 34. 

Bromlauge, 44. 

Brucine, 68. 

BUNSEN, 44. 

Butter, 18. 

Butyric acid, n-, 18. 


C. 


Cacodyl oxide, 17. 


test, 16, 17. 

Calcium acetate, 21. 
alkoxide of d-glucose, 35. 
benzoate, 47. 
carbamate, 45. 


INDEX. (3 


Calcium carbide, 23. 
citrate, 32. 
lactate, 31. 
oxalate, 27, 28. 
-oxide test, 3. 
potassium ferrocyanide, 41. 
racemate, 32. 
saccharate, 37. 
salicylate, 49, 60. 
tartrate, 32. 
Camphor, 61, 62. 
Artificial, 61. 
Camphoric acid, 62. 
Camphors, 61, 62. 
Cane-sugar. See sucrose. 
Caramel, 37. 
Carbamate, Calcium, 45. 
Carbamic acid, 45. 
Carbide, Calcium, 23. 
Carbolic acid. See phenol. 
Carbon, Allotropic modifications of, 
4, 5. 
Detection of, 1, 2. 
disulphide, 12, 43, 45. 
monoxide, 28. 
tetrachloride, 8. 
Carbonization, 1. 
Carbylamine, Ethyl-, 15. 
Methyl-, 12. 
reaction, 12, 51. 
Carbylamines, 12, 14, 15. 
Casein, 37, 61. 8 
Catechol, 57. 
Cellulose, 39, 40. 
Nitrates of, 39, 40. 
Ceratin, 69. 
Charcoal, Bone-, 4, 5. 
Wood-, 4. 
Chloral, 33. 
hydrate, 33. 
Chloride, Benzyl, 48. 
Chloroform, 3, 8, 25, 26, 33, 47. 
Chloropicrin, 60. 
Chloropropionie acid, a-, 31. 
Cinchona-bark, 61. 
Cinnamic acid, 54. 
Citrate, Calcium, 32. 
Citric acid, 32. 
Coagulation of albumin, 21, 69. 
Coal-gas, 1, 23. 
Coffee-beans, 61. 
Collodion, 40. 


SS EEE 
ee 


Colour-base of magenta, 62. 
Congo-red, 64, 
Copper acetylene, 23. 
albuminate, 69. 
alkoxide of d-glucose, 35. 
ammonium cyanurate, 43. 
oxalate, 28. 
CRAFTS. See FRIEDEL. 
Cresol, 50. 
Crystallization, 7. 
Cupric xanthate, 43. 
Cuprous xanthate, 43. 
Cyanate, Ammonium, 44. 
Potassium, 42, 44. 
Cyanic acid, 42. 
Cyanide, Potassium, 26, 40, 41, 42, 
60. 
silver, 40. 
Silver, 40, 41. 
Cyanurate, Copper ammonium, 45. 
Cyanuric acid, 45. 


D: 


Detection of carbon, 1, 2. 
halogens, 2, 3. 
hydrogen, 1, 2. 
nitrogen, 2. 
sulphur, 3, 4. 
Dextrin, 38. 
Diazo-aminobenzene, 56. 
-benzenesulphonie acid, p-, 59. 
Dibasic acids, Saturated, 27-30. 
Diethyl-amine hydrochloride, 13. 
-nitrosamine, 13. 
oxalate, 29. 
Dimethyl-amine, 14, 52. 
-aniline, 51. 
oxalate, 29. 
Dinitro-benzene, m-, 57, 58. 
o-, 58. 
p-, 58. 
-a-naphthol, 63. 
Dioses, 37, 38. 
Diphenyl-amine, 51. 
hydrochloride, 51. 
-urea, 52. 
Dippel’s oil, 65. 
Distillation, Fractional, 5. 
Steam, 5, 6. 
Dithiocarbamate, Ammonium, 45. 
Dyeing, 56, 60, 64, 67. 


74 INDEX. 


E. 


Elaïdie transformation, 24. 
Esters, 10, 11, 18-20. 
Ether, 6, II, 12. 
Ethers, 11, 12. 
Ethoxide, Sodium, g, 14. 
Ethyl acetate, 19, 20, 40. 
alcohol, 5, 9, ro, 11, 12, 17-20, 
22, 25, 26, 29, 43, 53, 69. 
Test for, 26. 
-amine hydrochloride, 13. 
benzoate, 53. 
-carbylamine, 15. 
chloride, 10. 
lactate, 31. 
-mercaptan, 12. 
nitrite, 13. 
-sulphate, Barium, 11. 
Potassium, 12, 14, 31. 
-sulphuric acid, 10, 11. 
Ethylene, 22, 23. 
bromide, 23. 
Extraction with solvents, 6. 


F. 


Fatty acids, Higher, 18, 19. 
Volatile, 18. 
FEHLING’S solution, 31, 32, 34, 37, 
38, 56 
Ferric acetate, 17. 
Basie, 17. 
succinate, Basic, 30. 
thiocyanate, 45. 
Ferricyanide, Potassium, 41, 42. 
Ferrocyanic acid, 41. 
Ferrocyanide, Potassium, 14, 40, 41, 
42, 52. 
calcium, 41. 
Fluorescein, 58. 
Formaldehyde, 21. 
“Formalin,” 21. 
Formate, Mercuric, 15, 16. 
Mercurous, 16. 
Potassium, 25, 27. 
Silver, 16. 
Sodium, 27. 
Formic acid, 15, 16, 17, 26, 30, 31, 
33 


Fractional distillation, 5. 
FRIEDEL and CRAFTS’ reaction, 47. 
Fructose, d-, 36. 


Furfuraldehyde, 34, 35. 
-hydrazone, 35. 
test, 34, 35. 
Fusel-oil, 9. 


G 


Galactose, d-, 36, 37. 

Gallie acid, 57. 

Gall-nuts, 61. 

Gelatine, 21, 60. 

Glucosazone, 34. 

Glucose, d-, 33, 34, 35, 36, 38. 
-sulphate, Barium, 35. 
-sulphuric acid, 35. 

Glycerol, 15, 18, 26, 27, 34, 66. 

Glycerose, 34. 

Glyceryl oleate, 24. 
tribenzoate, 27. 

Glyoxylic acid, 69. 

Graphite, 4. 

Gum-benzoin, 53. 

Guncotton, 40. 


EE 


Halogens, Detection of, 2, 3. 
Heterocyclic compounds, 65, 66. 
Hexodioses, 37, 38. 
Hexoses, 35, 36. 
Hydrochloric-acid test for, 35. 
““Humus substances,” 35. 
Hydrazobenzene, 52. 
Hydrocarbons, Saturated, 7-9. 
Unsaturated, 22-24. 
Hydrocyanic acid, 40, 41. 
Hydrogen, Detection of, 1, 2. 
Hydrolysis of nitriles, 15. 
Hydroxy-acids, 30-32. 
Hydroxyl-groups, Test for, 27, 31. 


I. 
Indigo, 67. 
-sulphonic acid, 67. 
-vatting, 67. 


Indophenin reaction, 66. 
Iodide, Benzyl, 48, 49. 
lodoform, 26. 

test, 13, 26. 
Tron ammonium tartrate, 31. 
Isatin, 66, 67. 
Isonitriles, 12, 14, 15. 


INDEX. 


Isopurpurate, Potassium, 60. 
Isopurpuric acid, 60. 


K. 


Ketone-alcohols. See sugars. 
Ketones, 21, 22. 
KJELDAHL’s method, 2. 


Kwop, 44. 


ie 


Laboratory methods, 5-7. 
Lactate, Calcium, 31. 
Ethyl, 31. 
Lactic acid, 30-32. 
Lactosazone, 38. 
Lactose, 36, 37, 38. 
Leevulinic acid, 35. 
LASSAIGNE’S test for nitrogen, 2, 26, 
Lead acetate, 4, 5, 18, 28. 
oleate, 25. 
oxalate, 28. 
““Lead-plaster,”’ 25. 
Lemons, 32. 
_Leuco-base of magenta, 63. 
LreBiG, 44. 
Lignin, Test for, 40. 
Linseed oil, 43. 
Litmus, 50. 


M. 


Magenta, 4, 21, 62, 63. 
Martius’ yellow, 63, 64. 
Melting-point, Determination of, 


07: 

Mercaptan, Ethyl-, 12. 

Mercuric formate, 15, 16. 

Mercurous formate, 16. 

Methane, 7, 8. 

Methyl alcohol, 29. 
-amine, 12, 14. 
-carbylamine, 12. 
-mustard-oil, 12. 
-nitrolic acid, 14. 

Method, KJELDAHL’s, 2. 

Methods, Laboratory, 5-7. 

Methylene chloride, 8. 

Milk, 37, 61. 

MILLon’s reagent, 69. 

Monobasic unsaturated acids, 24, 


is 


Monochlorobenzene, 48. 
Monoses, 33-36. 
Mucate, Potassium, 36. 
Mucic acid, 36, 37. 
Murexide, 46. 
test, 46. 

Mustard-oil, Methyl-, 12. 

reaction, 12. 


N. 


Naphthalene, 6, 7, 63. 
-monosulphonie acids, 63. 
picrate, 63. 

Naphthionate, Sodium, 64. 

Naphthionic acid, 64. 

Naphthol, 63. 

Naphthylamine, a-, 64. 

b-, 64. 

Nicotine, 67, 68. 

Nitraniline, p-, 61. 
hydrochloride, p-, 61. 

Nitrate, Urea, 44. 

Nitriles, 14, 15. 
Hydrolysis of, 15. 

Nitrite, Ethyl, 13. 

Nitro-benzene, 47, 48, 50, 52, 66, 67. 
-compounds, 14, 47. 
-methane, 14. 

Sodium, 14. 
-naphthalene, a-, 63. 
-phenol, o-, 59. 

p-, 59. 

-prusside test, 4. 
Nitrogen, Detection of, 2. 
Nitrolic-acid reaction, 14. 
Nitrosamine, Diethyl-, 13. 
Nitrosamines, 13. 
Nitroso-dimethylaniline. 51, 52. 

hydrochloride, 51, 52. 
-phenoxide, Sodium, 52. 

Nitrous-acid test, 13. 

Nitrous acid, Test for, 58. 





O. 
Oil. Almond, 24, 25. 
Dippel’s, 65. 
Linseed, 43. 


Turpentine, 61. 
Oleate, Glyceryl, 24. 

Lead, 25. 

Sodium, 24. 


76 INDEX. 


Olefines, 22, 23. 
Oleic acid, 24. 
Osazones, 34. 
Oxalate, Ammonium, 28. 
Calcium, 27, 28. 
Copper, 28, 29. 
ammonium, 29. 
Diethyl, 29. 
Dimethyl, 29. 
Lead, 28. 
Potassium, 27. 
ferric, 29. 
Sodium, 28. 
Urea, 44. 
Oxalates, Complex, 29. 
Oxalic acid, 7, 15, 26, 27-29, 44, 62. 
Oxamide, 29, 30. 
Oxanthranol, 64. 
Oxidation, 1, 3, 10, 16-18, 22. 


P: 


Paper, 40. 

Paraffin-wax, 8. 

Parchment-paper, 39. 

Pentoses, 34, 35. 

Petroleum, 5, 6, 8. 

Phenol, 49, 50, 55, 58-60, 62. 
-phthalein, 50, 58. 

Phenoxide, Sodium, 49. 

Phenyl-carbylamine, 52. 
-hydrazine, 34, 35, 37, 54, 56. 

hydrochloride, 56. 
Phenylenediamine, m-, 58. 


p-, 56. 

Phthalie acid, 58. 

- anhydride, 58. 

Picrate, Naphthalene, 63. 
Potassium, 59. 
Quinoline, 66. 

Picric acid, 50, 59, 60, 63, 65 -67. 

Pinene hydrochloride, 61. 

Polyoses, 38—40. 

Potassium acetate, 36. 
benzoate, 54, 55. 
calcium ferrocyanide, 41. 
cyanate, 42, 44. 
cyanide, 26, 40, 41, 42, 60. 
ethyisulphate, 12, 14, 31. 
ferricyanide, 41, 42. 
ferrocyanide, 14, 40, 41, 42, 52. 
formate, 25, 27. 


Potassium hydrogen saccharate, 36. 
tartrate, 31, 32. 

isopurpurate, 60. 

mucate, 36. 

oxalate, 27. 

picrate, 59. 

propionate, 15. 

rosolate, 62. 

silver cyanide, 40. 

tartrate, 31. 

thiocyanate, 42. 

urate, Di-, 46. 

xanthate, 43. 
Potato-starch, 39. 
Propionate, Potassium, 15. 
Propionic acid, 15. 
Propionitrile, 15. 
Prussian-blue test, 2, 40-42. 
Purpurate, Ammonium, 46. 
Pyridine, 65. 
Pyrogallol, 57. 
Pyrrole-red, 65. 


Q. 

Qualitative analysis of carbon com- - 

pounds, 1—4. 

Quinine, 61, 68. 
hydrochloride, 61, 67. 
sulphate, 67, 68. 

Quinol, 57. 

Quinoline, 66. 
dichromate, 67. 
hydrochloride, 66. 
picrate, 66. 


Re 


Racemate, Calcium, 32. 

Racemic acid, 32. 

Reaction, ADAMKIEWICz’s, 69. 
Biuret, 45, 69. 
Carbylamine, 12, 51. 
FRIEDEL and CRAFTS’, 47. 
Indophenin, 66. 
Nitrolic-acid, 14. 
SCHIFF’s, 21. 
Xanthoprotein, 69. 

Reagent, MirLON’s, 69. 
ScHIFF’S, 21. 
SCHWEITZER’S, 39. 

Reagents, Alkaloid-, 65, 67. 

Rectified spirit, 5, 10. 


INDEX. 77 


Resin, Aldehyde-, 20. 
Resorcinol, 36, 57, 58. 
Rosolate, Potassium, 62. 
Rosolic acid, 62. 


S. 


Saccharate, Calcium, 37. 
Potassium hydrogen, 36. 

Salicylate, Calcium, 49, 60. 

Salicylic acid, 6, 60. 

Salting-out, 68. 

“Salt of sorrel,’’ 29. 

“‘Sand-sugar.”’ See lactose. 

Saponification, 18, 19, 24. 

Saturated acids, CnH.nO,, 18-20. 
dibasic acids, 27-30. 
hydrocarbons, 7-9. 

ScuHIFF’s reaction, 21. 
reagent, 21. 

SCHOTTEN's test for hydroxyl- 

groups, BAUMANN and, 27. 

ScHWEITZER’S reagent, 39. 

Silver acetate, 17. 
acetylene, 23. 
cyanide, 40, 41. 
formate, 16. 

-mirror test, 20, 30, 33, 54. 
potassium cyanide, 40. 
thiocyanate, 42, 43. 

SKRAUP’S synthesis, 66. 

Smokeless powder, 40, 

Soap, 18, 19. 

Sodium acetate, 7, 17, 56. 
anthraquinonesulphonate, 64. 
benzenesulphonate, 47, 49, 52. 
ethoxide, 9, 14. 
formate, 27. 
naphthionate, 64. 
nitromethane, 14. 
nitrosophenoxide, 52. 
oleaté, 24. 
oxalate, 28. 
phenoxide, 49. 

Solvents, Extraction with, 6. 

Spirit, Rectified, 5, ro. 

Starch, 38, 39: 

Barium alkoxide of, 38. 
-paste, 38. 
Potato-, 39. 
Test for, 38. 
Steam distillation, 5, 6. 


Strychnine, 68. 
nitrate, 68. 
Succinate, Barium, 30. 
Basic ferric, 30. 
Succinic acid, 30. 
Succinimide, 30. 
Sucrose, 1, 34, 37. 
Sugar. See sucrose. 
Cane-. See sucrose. 
Sugars, 33-40. 
Sulphanilic acid, 59. 
Sulphur, Detection of, 3, 4. 


fie 


Tannin, 60, 61, 65, 67. 

Tartar emetic, 32. 

Tartaric acid, 31, 32. 

Tartrate, Calcium, 32. 

Iron ammonium, 31. 
Potassium, 31. 
hydrogen, 31, 32. 

Terpenes, 61. 

Test, BEILSTEIN’S, 2, 3, 10, 31. 
Cacodyl, 16, 17. 
Calcium-oxide, 3. 

CARIUS’, 3. 
Caustic-alkali, 3. 
Furfuraldehyde, 34, 35. 
Todoform, 13, 26. 
KSJELDAHL’S, 2. 
LASSAIGNE’S, 2, 26. 
Murexide, 46. 
Mustard-oil, 12. 
Nitroprusside, 4. 
Nitrous-acid, 13. 
Prussian-blue, 2, 40, 42. 
Silver-mirror, 20, 30, 33, 54. 
WirL and VARRENTRAP’S, 2. 
for acetic acid, 17, 22. 
acetone, 21. 
anthraquinone, 64. 
antipyrine, 66. 
brucine, 68. 
ethyl alcohol, 26. 
hexoses, Hydrochloric-acid, 35. 
hydroxyl-groups, 27, 31. 
lignin, 40. 
naphthylamines, 64. 
nitrous acid, m-Phenylenedi- 
amine, 58. 
phenol, Ferric-chloride, 49. 


78 INDEX. 


Test for primary amines, 12. 

pyridine, 65. 

salicylic acid, 60. 

starch, 38. 

strychnine, 68. 

tannin, 60, 61. 

the double bond,von BAEYER’S, 

23, 24, 47, 65. 

water in alcohol, 9, 10. 
Tests for albumin, 69. 

aniline, 51. 

carbon, 1, 2. 

halogens, 2, 3. 

hydrogen, 1, 2. 

nitrogen, 2. 

sulphur, 3, 4. 
Tetramethylalloxantine, 46. 
Thioeyanate, Ammonium, 3, 45. 

Ferric, 45. 

Potassium, 42. 

Silver, 42, 43. 

Thiophen, 66. 

Toluene, 48. 
Transformation, Elaidic, 24. 
Tribromo-aniline, 51. 

-phenol, 49. 

-resorcinol, 57. 
Trimethylamine, 14. 
Triphenylmethane, 47. 
Trithiocarbonate, Barium, 43. 
Turpentine, Oil of, 61. 





U. 
Unsaturated acids, Monobasic, 24, 


Dos 
hydrocarbons, 22-24. 
Urate, Ammonium, 46. 
Di-potassium, 46. 
Urea, 6, 44, 45, 52. 
nitrate, 44. 
oxalate, 44. 
Uric acid, 46. 
Urine, 36, 44-46. 
Estimation of urea in, 44, 45. 


Ve 
VARRENTRAP’S method, Wirr and, 
2. 


W. 


Wax, Paraffin-, 8. 
Wii and VARRENTRAP’s method, 2. 
Wine, 9. 
WOHLER’S synthesis of urea, 44. 
Wood, 27. 

-charcoal, 4. 


X. 


Xanthate, Cupric, 43. 
Cuprous, 43. 
Potassium, 43. 
Xanthoprotein reaction, 69. 








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Mixter’s Elementary Text-book of Chemistry. .................0000. I2mo, 
Morgan’s An Outline of the Theory of Solutions and its Results....... I2mo, 
blementsiof Piysical Chemistry... 6. 020 ccs a ete eene see veererelens I2mo, 

* Physical Chemistry for Electrical Engineers.................. I2mo, 
Morse’s Calculations used in Cane-sugar Factories. ......... 16mo, morocco, 
Mulliken’s General Method for the Identification of Pure Organic Compounds. 
, WGI Vie EA AEG vr Pay aI Sr et ome tee ene Large 8vo, 
O’Brine’s Laboratory Guide in Chemical Analysis...............e..... 8vo, 
O’Driscoll’s Notes on the Treatment of Gold Ores. .................... 8vo, 
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“¢ fs ry Oe Part Two. (Turnbull. ). TA, 12mo, 


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8vo, paper, 
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Pinner’s Introduction to Organic Chemistry. (Austen.).............. I2mo.- 
Beale NEE Id ME 6 sass) < + vai sis singin Sole ofa saimyehs ee este ues 8vo, 
Prescott and Winslow’s Elements of Water Bacteriology, with Special Refer- 

BHCEMOROATIICAT YS VY ATCE ANALYSIS. ann ccc ou in pies snene een bom spe I2mo, 
REISE GATIGULO PIECE A VEIND na eneen 0 ses 2 obs ene is a, es m8 6 washes 8vo, 


Richards and Woodman’s Air, Water, and Food from a Sanitary Standpoint. .8vo, 
Ricketts and Russell’s Skeleton Notes upon Inorganic Chemistry. (Part I 


TVOT HONG CAI Blemenfs).,...…. oye en oes wed oe waas 8vo, morocco, 
Rickersand Millers Notes on ASSAYING. .......0.066+06405 ere wms cere 8vo, 
Rideal’s Sewage and the Bacterial Purification of Sewage.............. 8vo, 

Disinfection and the Preservation of Food... ..............0e000. 8vo, 
Riggs’s Elementary Manual for the Chemical Laboratory.............. 8vo, 
Robine and Lenglen’s Cyanide Industry. (Le Clerc.)................. 8vo, 
Rostoski's Serum Diagnosis. (Bolduan.). .….......…..........eee.: I2mo, 
Ruddiman’s Incompatibilities in Prescriptions. ...................000- 8vo, 
NEEN Nn 12 m0, 
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Salkowski’s Physiological and Pathological Chemistry. (Orndorff.).....8vo, 
Schimpf’s Text-book of Volumetric Analysis. .…..................…. I2mo, 

Essentials of Volumetric Analysis. ..........…........ RAON ee Iz2mo, 
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Smith’s Lecture Notes on Chemistry for Dental Students. ... .......... 8vo, 
Spencer’s Handbook for Chemists of Beet-sugar Houses. ....16mo, morocco. 

Handbook for Cane Sugar Manufacturers.............. 16mo, morocco, 
Moen Ee sek OCICS ATI SOLS, nato eile tla lette aoa earn «ect die « ardens aje a4 8vo, 
TeEriiman sebiementaryilseSsSOns in Heat. .‚ oan sl ela 0 eeens eeen 8vo, 
Rn estriotive GenerdhGheimistry. e.o spans ao so 0 8vo, 
Treadweils Oualitative Analysis. (Hall)... ecu oe te meen we on 8vo, 

OCT PO LUV OP ASIOUYSIG= 6 (ILA eo too ocars 4 ousnns sg cie-dnirnie 6.5 eusin oi ahe 9 aye 8vo, 
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Washington’s Manual of the Chemical Analysis of Rocks...........:.. 8vo, 


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Wassermann’s Immune Sera: Heemolysins, Cytotoxins, and Precipitins. (Bol- 


duane eee ee pee ee I2mo, 
‘Weaver's Military Explosives... 00 0...) Pi eee 8vo, 
Wehrenfennig’s Analysis and Softening of Boiler Feed-Water 8vo 
Wells’s Laboratory Guide in Qualitative Chemical Analysis.) sia nne 8vo, 
Short Course in Inorganic Qualitative Chemical Analysis for Engineering 
Students. 5 uit teer a che he I2mo, 
Text-book of: Chemical Arithmetic 2% tas. enten en eee eee I2mo, 
‘Whipple’s Microscopy of Drinking-water. ..\................,...0 ue 8vo, 
Wilson's Cyanide Processes. 93.0 4 )4y MAU ee I2mo, 
Chiorination: Process.) 05... 40 oe ee ee eee Izmo, 
Winton’s Microscopy of Vegetable Foods. .…. 8vo, 
Wulling’s Elementary Course in Inorganic, Pharmaceutical, and Medical 
Chemistry las vatte Sed, co na nk eg I2mo, 


CIVIL ENGINEERING. 


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BRIDGES AND ROOFS. HYDRAULICS. MATERIALS OF ENGINEERING. 


KAILWAY ENGINEERING. 


‘Baker's Engineers’ Surveying Iestruments. .. … eeen I2mo, 
Bixby’s Graphical Computing Table................ Paper 194 24} inches. 
stk Burr’s Ancient and Modern Engineering and the Isthmian Cana. (Postage, 
27 cents additional), ....v....- «ss en en 8vo, 
“Comstock’s Field Astronomy for Engineers vene ne Ee en 8vo, 
Davis’s Elevation and Stadia Tables... sn 4%. Jas ee eee 8vo, 
Elliott’s. Engineering for Land’ Drainage nen nen I2mo, 
Practical Farm Drainage. !s 5.122). 6 oe. En I2mo, 
“*Fiebeger’s Treatise on Civil Engineering....................e00e0-0- 8vo, 
“Flemer’s Phototopographic Methods and Instruments................. 8vo, 
Folwell’s Sewerage. (Designing and Maintenance.)................... 8vo, 
“¥reitag’s Architectural Engineering. 2d Edition, Rewritten........... 8vo, 
“French and Ives’s Stereotomy. …… <a. en ee =e en 8vo, 
“Goodhue’s Municipal Improvements... neen een I2mo, 
“Goodrich’s Economic Disposal of Towns’ Refuse.............. alin es eee 8vo, 
*Gore’s Elements of Geodesy. . .… . 20 ane meere nn = penis ane 8vo, 
- Hayford’s Text-book of Geodetic Astronomy. © . weten tan ee 8vo, 
‘Hering’s Ready Reference Tables (Conversion Factors). ..... 16mo, morocco, 
Wowe’s Retaining Walls for Earth. .......….... verder eenen I2mo, 
* Ives’s Adjustments of the Engineer’s Transit and Level.......... 16mo, Bds. 
Ives and Hilts’s Problems in Surveying................... 16mo, morocco, 
‘Johnson’s (J. B.) Theory and Practice of Surveying.............. Small 8vo, 
Johnson’s (L. J.) Statics by Algebraic and Graphic Methods. ........... 8vo, 
Laplace’s Philosophical Essay on Probabilities. (Truscott and Emory.).12mo, 
Mahan’s Treatise on Civil Engineering. (1873.) (Wood.)............ 8vo, 
* “Descriptive Geometry... a. nasa los eran lede en 8vo, 
Merriman’s Elements of Precise Surveying and Geodesy............... 8vo, 
Merriman and Brooks’s Handbook for Surveyors........... 16mo, morocco, 
Nugent’s Plane Surveying. ...... „nr ++ +» = aam ee 8vo, 
Ogden’s Sewer Design, nr +> us - 00s = as ape pa ea I2mo, 
Parsons’s Disposal of Municipal Refuse. . ....... 1... oor succes pine 8vo, 
Patton’s Treatise on Civil Engineering...... a ae gee ee 8vo half leather, 
Reed’s Topographical Drawing and Sketching ................. bne 4to, 
Rideal’s Sewage and the Bacterial Purification of Sewage.............. 8vo, 
Siebert and Biggin’s Modern Stone-cutting and Masonry. .............. 8vo, 
Smith's Manual of Topographical Drawing. (McMillan.).............. 8vo, 
Sondericker’s Graphic Statics, with Applications to Trusses, Beams, and Arches, 
8vo, 


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Taylor and Thompson’s Treatise on Concrete, Plain and Reinforcea.....8vo, 
* Trautwine’s Civil Engineer’s Pocket-book................ 16mo, morocco, 
Venable’s Garbage Crematories in America. ...... eneen 8vo, 
Wait’s Engineering and Architectural Jurisprudence.................. 8vo, 
Sheep, 

Law of Operations Preliminary to Construction in Engineering and Archi- 
RU on en B Bn OR RO RAN 8vo, 

Sheep, 

DENON GCORLFECIS NEE EE ANDA ETE ee hek bels ed 8vo, 
Warren’s Stereotomy— Problems in Stone-cutting.....°............... 8vo, 


Webb’s Problems in the Use and Adjustment of Engineering Instruments. 
16mo, morocco, 


AMO LOO CTA D 1G, SUL VO WIN gs eren. ront wek eo marani Le OT Bale hk > 8vo, 


BRIDGES AND ROOFS. 


Boller’s Practical Treatise on the Construction of Iron Highway Bridges. .8vo, 
MEET MOSHRAVeT  ETLOVC. wits ss fae ssc ct See deka eee 4to, paper, 
Burr’s Course on the Stresses in Bridges and Roof Trusses, Arched Ribs, and 
NETO AN Le) SAE dM ee el ES 8vo, 
Burr and Falk’s Influence Lines for Bridge and Roof Computations...... 8vo, 
Design and Construction of Metallic Bridges ..................... 8vo, 
Du Bois’s Mechanics of Engineering. Vol. Il.....................€mall 4to, 
Foster’s Treatise on Wooden Trestle Bridges..................-.....e. 4to, 
howler Order MOUNGATIONS „nnn vereren ie enten He ale eles ee eee Svo, 
OEE eT RS TEE ae ee re Dde eeen ee 8vo, 
En Ag ee AR EEE RTE ace ache oi 8vo, 
ArcheskanWwoodsltonvandsiSstonenn. ote. ee ee he es sets eee ane 8vo, 
Hawa seureatise OMEATCHES Wim IA rene eea eager 8vo, 
Design of Simple Roof-trusses in Wood and Steel. ................ 8vo, 
er Mot En ei RAe 8vo, 
Johnson, Bryan, and Turneaure’s Theory and Practice in tke Designing of 
Mrodenmemiranred SLEUCtUres den SRT ate a eee pe ee Small 4to, 
Merriman and Jacoby’s Text-book on Roofs and Bridges: 
Dan Stressesnnasimplel TFUsses. PEP. o.a aoe are er suelo Kn 8vo, 
Part 1. Graphic: Statics’). ..--...-... yee Shun eae Re Pe ey 
Den OEE YOUN ee ec aici ee edi eo oe Sep eine ee base, pee RENE 
Pee Bers RUCOULES Gos 6 Sie ete ee cue iT eelde ene ee ao aye kala cm 8vo, 
Morisons Memphis Bridge... .....:........ tee ees 4to, 
Waddell’s De Pontibus, a Pocket-book for Bridge Engineers. .16r-0, morocco, 
miSnecineationg tor steel Bridges. .… ............ ns eme voe I2mo, 
Wright’s Designing of Draw-spans. Two parts in one volume.......... „8vo, 
HYDRAULICS, 
Bent eer OMIT ALONG sa ene ltteers lar SO OR LRE 8vo, 
Bazin’s Experiments upon the Contraction of the Liquid Vein Issuing from 
an Orifice. (Trautwine.) PE ee ee ERE NEL EREN Or 8vo, 
Hover Treatise on Hydraulics. oi... Jonatan ate lee aten bie ole 8vo, 
Church’s Mechanics of Engineering. ...........0.. ese enne 8vo, 
Diagrams of Mean Velocity of Water in Open Channels.......... paper, 
BED MOROEE (50; mr ADR AR oe a aa ale PE ee 8vo, 
Coffin’s Graphical Solution of Hydraulic Problems.......... 16mo, morocco, 
Flather’s Dynamometers, and the Measurement of Power..........-. I2mo, 
Folwell’s Water-supply Engineering. ... ..…....... eere ee tare BEREN 8vo, 


Piet HIRAI OOWOE. fs vaandel Fu op cleo ensen ee angke ete 8vo, 


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‘Fuertes’s Water and Public Health, ‚over «cad sven oen ernestine a SA set2mo; 


Water-filtration, Works... os...) vote ee ee eee bale E20 
Ganguillet and Kutter’s General Formula for the Uniform Flow of Water in 
Rivers and Other Channels. (Hering and Trautwine.)........ 8vo, 

Hazen’s Filtration of Public Water-supply. «ann ee ee en 8vo, 
Hazlehurst’s Towers and Tanks for Water-works. .................... 8vo, 
Herschel’s 115 Experiments on the Carrying Capacity of Large, Riveted, Metal 
Conduits. fm heb Adr AE Ten EEEN 8vo, 

Mason’s Water-supply. (Considered Principally from a Sanitary Standpoint.) 
8vo, 

Merriman’s Treatise’on, Hydraulics: jcanisic ek ba. Se ee ee eee 8vo, 
* Michie’s Elements of Analytical Mechanics.................2+-.+-%: 8vo, 
Schuyler’s Reservoirs for Irrigation, Water-power, and Domestic Water- 
Stppl yi. dein hla ED Rn Large 8vo, 

“ek Thomas and Watt’s Improvement of Rivers. (Post., 44c. additional.) 4to, 
Turneaure and Russell’s Public Water-supplies.....................- 8vo, 
Wegmann’s Design and Construction of Dams.....................-.-- 4to, 
Water-supply of the City of New York from 1658 to 1895.......... Ato, 
Williams) and,Hazen’s Hydraulic Tables. ...... naer 8vo, 
Wilson’s Irrigation Engineeringss sies snor sce Oe Small 8vo, 
Wolff’s Windmill as a Prime Mover..................02.005 Enige 8vo, 
Wood’s Turbines. „are santi rte ants dre EEE 8vo, 
Elements of Analytical Mechanics... 7. vatetene Ane eee 8vo, 


MATERIALS OF ENGINEERING. 


Baker's Treatise on Masonry Construction. ‚nen Me ee 8vo, 
Roads and Pavements. 4. tannansnere clea) sls ee he eee eee 8vo, 
Black’s. United. States Public Workser tere en Oblong 4to, 
* Bovey’s Strength of Materials and Theory of Structures.............. 8vo, 
Burr’s Elasticity and Resistance of the Materials of Engineering. ...... 8vo, 
Byrne's Highway Construction. ...........<- +. anys esi ee 8vo, 
Inspection of the Materials and Workmanship Employed in Construction. 
16mo, 

Church’s Mechanics of Engineering: ../. =. 0: «+ salsa slain ae 8vo, 
Du Bois’s Mechanics of Engineering. Vol. lee Small ato, 
*Eckel’s Cements, Limes, and Plasters............... wey ee hore a 8vo, 
Johnson's Materials of, Construction. „nr eee ae Large 8vo, 
Fowler’s Ordinary Foundations... operante su: seacoast anne eee 8vo, 
Graves's Forest-Mensuration Ss ars donner see ee oe 8vo, 
*‘Greene’s ‘Structural: Mechanics... ntt en pane eas |. 8vo, 
Keeps Cast Ironi eo tac eee es eren ree Bs te PO ep Sham eo. 8vo, 
Lanza’s Applied. Mechanics. somt neko ene ee ee eee ee 8vo, 
Marten’s Handbook on Testing Materials. (Henning.) 2vols......... 8vo, 
Maurer’s Technical Mechanics, 2.03.52. - 3. ee oe eee 8vo, 
Merrill’s Stones for Building and Decoration. . ....................-- 8vo, 
Merriman’s' Mechanics of Materials. nn nt «sce ee 8vo, 
Strength of Materials „2 sar. Siet ie ee eee MO so eee I2mo, 
Metcalf’s Steel.. A Manual for Steel-users. .. ore So gee eee I2mo, 
Patton’s Practical Treatise on Foundations... —a en ee 8vo, 
Richardson’s Modern Asphalt Pavements. .............0...2.04++0-5 8vo, 
Richey’s Handbook for Superintendents of Construction.......... r6mo, mor., 
* Ries’s Clays: Their Occurrence, Properties, and Uses................ 8vo, 
Rockwell’s Roads and Pavements in France. .................+-+--- I2mo, 
Sabin’s Industrial and Artistic Technology of Paints and Varnish.. . .8vo, 
‘Smith’s Materials of Machines... a. te seren Suge Eee alta 
Snow’s Principal Species of Wood, .…… varen 8vo, 


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Spalding’s Hydraulic Cement.......... hr ete ROGET ae ete zich 12m0, 


Texg-book RR derand Pavement... 00... ties te kancea cae eee I2mo, 
Taylor and Thompson’s Treatise on Concrete. Plain and Reinforced...... 8vo, 
Thurston’s Materials of Engineering. 3 Parts.....................6.. 8vo, 

Part 1. Non-metallic Materials of Engineering and Metallurgy..... 8vo, 

Lope bial OTE a] Ls rr i aia 8vo, 

Part III. A Treatise on Brasses, Bronzes, and Other Alloys and their 

kn EB oe ne Sk are Chass awicedreeaceccueecn 8vo, 
Thurston’s Text-book of the Materials of Construction. ................ 8vo, 
Tillson’s Street Pavements and Paving Materials...................... 8vo, 
Waddell’s De Pontibus (A Pocket-book for Bridge Engineers.)..16mo, mor., 

Spectncaunons torsteel Bridges. … 5... ot. malen eaten vee ae ee I2mo, 

Wood’s (De V.) Treatise on the Resistance of Materials, and an Appendix on 
POEM LECenVaiOr Obl Ember. Jant sic Mie Secs vue wre eres nee 8vo, 
Wood’s (De V.) Elements of Anatytical Mechanics.................... 8vo, 
Wood’s (M. P.) Rustless Coatings: Corrosion and Electrolysis of Iron and 
ad aen PR ties Cae SET EE Oe set mekiatgrees 8vo, 


RAILWAY ENGINEERING. 


Andrew’s Handbook for Street Railway Engineers... ..3x5 inches, morocco, 
Berg’s Buildings and Structures of American Railroads................ 4to, 
Brook’s Handbook of Street Railroad Location. , ........... 16mo, morocco, 
Buit’s Civil Ensineer’s Field-book., . 0.06 …… nr a aen eee 16mo, morocco, 
ed al su raMStTLOM-CUNVEs «cu cs nt cus Secale bidua.s sere woe & ids 16mo, morocco, 
Railway and Other Earthwork Tables....................- Rae OVO 
Dawson’s “Engineering” and Electric Traction Pocket-book. .16mo, morccco, 
Dredge’s History of the Pennsylvania Railroad: (1879).............. Paper, 
* Drinker’s Tunnelling, Explosive Compounds, and Rock Drills. 4to, half mor., 
raven cela pleat Chie Mards....….... arne eeen Oe ene Cardboard, 
Godwin’s Railroad Engineers’ Field-book and Explorers’ Guide. ..16mo, mor., 
Howard’s Transition Curve Field-book.................... 16mo, morocco, 
Hudson’s Tables for Calculating the Cubic Contents of Excavations and Em- 
EERE Te Ol ER EE NE EREN Ree ag ae 8vo, 

Molitor and Beard’s Manual for Resident Engineers. . ............... 16mo, 
Nagle's Field Manual for Railroad Engineers. ...… ….....…. 16mo, morocco, 
Philbrick’s Field Manual for Engineers.................... 16mo, morocco, 
Geur a Se Tela BAaelneerlng. ie cies ns vcs sees ale ens 2,09 16mo, morocco, 
Ee mM ERAN IEG newer Pine, nat ors Gacepe a 1c. sys ale piso leu o/aigieelo as: aii 16mo, morocco, 
Taylor’s Prismoidal Formule and Earthwork. ,.. ............ nen 8vo, 
* Trautwine’s Method ot Calculating the Cube Contents of Excavations and 
Embankments by the Aid of Diagrams. ..................... 8vo, 


The Field Practice of Laying Out Circular Curves for Railroads. 


I2mo, morocco, 

ECR ED ARTIS IC OES oe NN Paper, 
Webbs Railroad Construction. ts stan. Ede deet eh deed e- 16mo, morocco, 
Economics of Railroad Construction.................. ..Large 12mo, 
Wellington’s Economic Theory of the Location of Railways. ....Small 8vo. 

DRAWING. 

eneen oo edu Elektr an io cca cic sie a 0 8 6» oo ss cya dhe gw lalate ecqiaacele 8vo 
EROL EROIGCHaTiCal Dra Wwill@a ate cick iis zen ease « diecsdeus weke s+ a en wis, 8vo, 
* xe = ie Abridged LA os at relates an abi 8vo, 
EEEN OF DrAWINE ver ces agen ree cls tie Dialers sans 8vo, paper, 





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Coolidge and Freeman’s Elements of General Drafting for Mechanical Engi- 


FLO ON Ba a a sie Joy save tel als! ole bey a oso ute Seance NN Oblong 4to, 
Durley's Kinematics of Machines... i ...,.0...% Eee 8vo, 
Emch’s Introduction to Projective Geometry and its Applications........ 8vo, 
Hill's Text-book on Shades and Shadows, and Perspective........ erf CEVO 
Jamison’s Elements of Mechanical Drawing, . rme isn ONO, 
Advanced Mechanical Drawing............ Ee susan praatte SMO 
Jones’s Machine Design: 
Part I. Kinematics of Machinery. … … ad nn Pettson Ae 8vo, 
Part II. Form, Strength, and Proportions of Parts. .… 8vo, 
MacCord’s Elements of Descriptive Geometry... 5 fe eee RC 8vo, 
Kinematics; or, Practical Mechanism. …. ee 8vo, 
Mechanical Drawing, sc nn san zen onse ene nae en 4to, 
Velocity Diagrams, . |... 20s» seine en sinene el ene 8vo, 
MacLeod’s Descriptive Geometry.. ........ eee IR. Small 8vo, 
* Mahan’s Descriptive Geometry and Sione-cutting. en ad Ve 
Industrial Drawing. (Thompson), nv 8vo, 
Moyer's Descriptive Geometry.. nan +2222 8vo, 
Reed’s Topographical Drawing and Sketching, „st 4to, 
Reid’s Course in'Mechanical Drawing. .…… 445 eee 8vo, 
Text-book of Mechanical Drawing and Elementary Machine Design. 8vo, 
Robinson's Principles of Mechanism... .-.. :...4.2 50.5 ae 8vo, 
Schwamb and Merrill’s Elements of Mechanism...................... 8vo, 
Smith’s (R. S.) Manual of Topographical Drawing. (McMillan.).......8vo, 
Smith (A. W.) and Marx's Ì achine Design... 8vo, 
* Titsworth’s Elements of Mechanical Drawing................ Oblong 8vo, 
Warren’s Elements of Plane and Solid Free-hand Geometrical Drawing. 12mo, 
Drafting Instruments and Operations. ,…… nn I2mo, 
Manual of Elementary Projection Drawing..................... I2mo, 
Manual of Elementary Problems in the Linear Perspective of Form and 
BDAC OW sonen een en pad 6 sel eee er I2mo, 
Plane Problems in Elementary Geometry............ re I2mo, 
Primary Geometry. manen ca eee ee I2mo, 
Elements of Descriptive Geometry, Shadows, and Perspective. ..... .8vo, 
General Problems of Shades and Shadows. ..................... 8vo, 
Elements of Machine Construction and Drawing. … 8vo, 
Problems, Theorems, and Examples in Descriptive Geometry...... 8vo, 
Weisbach’s Kinematics and Power of Transmission. (Hermann and 
Klein.) oe wk kha ee scm ee ee ee ee 8vo, 
Whelpley’s Practical Instruction in the Art of Letter Engraving. ...... I2mo, 
Wilson’s (H. M.) Topographic Surveying. ..:. 1:1; ))) 2S) S eee 8vo, 
Wilson's (V. T.) Free-hand Perspective. :. ne 8vo, 
Wilson’s (V. T.) Free-hand Lettering.......... trae ee te te te ee 8vo, 
Woolf’s Elementary Course in Descriptive Geometry............. Large 8vo, 


ELECTRICITY AND PHYSICS. 


Anthony and Brackett’s Text-book of Physics. (Magie.)......... Small 8vo, 
Anthony’s Lecture-notes on the Theory of Electrical Measurements... . I2mo, 
Benjamin’s History of Electricity. ........:..:.... «s)eeieeeee EN 8vo, 
Voltaic Cell, … . wan eea an en te ete 8vo, 
Classen’s Quantitative Chemical Analysis by Electrolysis. (Boltwood.). 8vo, 
* Collins’s Manual of Wireless Telegraphy.. … as ssn) gee I2mo, 
Morocco, 

Crehore and Squier’s Polarizing Photo-chronograph................... 8vo, 


Dawson’s “Engineering” and Electric Traction Pocket-book.16mo, morocco, 


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Dolezalek’s Theory of the Lead Accumulator (Storage Battery). (Von 


en A I2mo, 
Duhem’s Thermodynamics and Chemistry. (Burgess.)................ 8vo, 
Flather’s Dynamometers, and the Measurement of Power............ I2mo, 
GalnenDernMaegnetensm(Mottelay.): .-.. ar tardene o overshot ore sierelle «actu ales 8vo, 
Hanchett’s Alternating Currents Explained.....................000- I2mo, 
Hering’s Ready Reference Tables (Conversion Factors)...... 16mo, morocco, 
Holman’s Precision of Measurements... ................. eee 8vo, 
Telescopic Mirror-scale Method, Adjustments, and Tests....Large 8vo, 
Kinzbrunner’s Testing of Continuous-current Machines............... 8vo, 
MANN AUCTS specteumsAnalvsis: (Tingle.)..……. nn. oto Hote Koeler over 8vo, 
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* Parshall and Hobart’s Electric Machine Design.......... 4to, half morocco, 
* Rosenberg’s Electrical Engineering. (Haldane Gee—Kinzbrunner.). . .8vo, 
Ryan, Norris, and Hoxie’s Electrical Machinery. Vol. I............... 8vo, 
Whurston Sy StatlOnary Steam=engines. 2. 5... . siens ecsisve e ble ee vce 8vo, 
name aiementary Lessons in Heat. .….. . + … ooo sists ad onweders 8 8vo, 
Tory and Pitcher’s Manual of Laboratory Physics............. „Small 8vo, 
Ulke’s Modern Electrolytic Copper Refining... ......... ccc eee eee eee 8vo, 
LAW. 
PISA ISIS LO MIENTS OL aWe oc. eee eae bee be cb cee sense ded wan 8vo, 
* Treatise on the Military Law of United States.................... 8vo, 
* ; Sheep, 
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; Sheep, 
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Sheep, 
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Encyclopedia of Founding and Dictionary of Foundry Terms Used in the 
Practice of Moulding............ oki ann Warie Dats a I2mo, 
Claassen’s Beet-sugar Manufacture. (Hall and Rolfe.)................ 8vo, 
mEekelsCementssbimes tand Plasters: 24 soe, « on sie nie wie ein os enn wed 8vo, 
Mesters ModerarEiohsBrplosives. 40°. + 6 6 causie His. sei eingeve: ble en 0,00 ble ee 8vo, 
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Hora boler Making for Boiler Makers... . seer eieren ea voce 00s z&mo, 
Manen ac Honets. Handbook. „a.s s een deine dae en hheaend 8vo, 
POOR SGRSEUTOL sels vs abet see eee. DV nt te etnies sedert We 


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Leach’s The Inspection and Analysis of Food with Special Reference to State 


Controle sir tenere kee oe aie Re Large 8vo, 
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Morse’s Calculations. used in Cane-sugar Factories. ......... 16mo, morocco, 
* Reisig’s Guide to Piece-dyeing. .......... eee eee seen nennen enn ere 8vo, 
Rice’s ‘Concrete-block Manufacture. . so ste ve + +> + 0 00 bles © hie eels sige 8vo, 
Sabin’s Industrial and Artistic T echnology of Paints and Varnish........ 8vo, 
Smith’s Press-working of Metals. .........--- ee eee esse reer ctereeree 8vo, 
Spalding’s Hydraulic Cement.........---.5.-.-.+++ +> segue sme ees 12mo, 
Spencer’s Handbook for Chemists of Beet-sugar Houses. .... 16mo, morocco, 

Handbook for Cane Sugat Manufacturers.............. x6mo, morocco, 
Taylor and Thompson’s Treatise on Concrete, Plain and Reinforced... .. 8vo, 
Thurston’s Manual of Steam-boilers, their Designs, Construction and Opera- 

tion. ees oo re Boks ies Bie aranka veelen aati te 8vo, 
* Walke’s Lectures on Explosives.............eeese eneen eeer ennen 8vo, 
Ware’s Beet-sugar Manufacture and Refining...............-+:. Small 8vo, 
Weaver’s Military Explosives.:.n 24... oe oneens 5 yt ¢ oon cae ee 8vo, 
West’s American Foundry Practice..............senee eene eenen en I2mo, 

Moulder’s Tezt-book. stele ee Detects ousus oe eee I2mo, 
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MATHEMATICS. 

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Briggs’s Elements of Plane Analytic Geometry............---+++.-+- I2mo, 
“Compton’s Manual of Logarithmic Computations..............+.-+.+- I2mo, 
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* Introduction to the Theory of Algebraic Equations......... Large 12mo, 
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Elementary Synthetic Geometry. .. . … ..... eenen eneen neren 8vo, 

Rational Geometry: ...°) 280.) 254 one nn a oe een I2mo, 


* Johnson’s (J. B.) Three-place Logarithmic Tables: Vest-pocket size. paper, 
roo copies for 

% Mounted on heavy cardboard, 8 X 10 inches, 
ro copies for 

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Elementary Treatise on the Integral Calculus.......... ... Small 8vo, 
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Small 8vo, 


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Manning’s Irrational Numbers and their Representation by Sequences and Series 
I2mo 


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Mathematical Monographs. Edited by Mansfield Merriman and Robert 


O5 NIECE ita, Sn rr ENEN TEN .Octavo, each 


No. 1. History of Modern Mathematics, by David Eugene Smith. 
No. 2. Synthetic Projective Geometry, by George Bruce Halsted. 
No. 3. Determinants. by Laenas Gifford Weld. No. 4. Hyper- 
bolic Functions, by James McMahon. No. 5. Harmonic Func- 
tions, by William E. Byerly. No.6. Grassmann’s Space Analysis, 
by Edward W. Hyde. No. 7. Probability and Theory of Errors, 
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by Alexander Macfarlane. No. 9g. Differential Equations, by 
William Woolsey Johnson. No. 10. The Solution of Equations, 
by Mansfield Merriman. No. rr. Functions of a Complex Variable, 
by Thomas S. Fiske. 


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Wood’s Elements of Co-ordinate Geometry. ... ............. ee. 8vo, 
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MECHANICAL ENGINEERING. 


MATERIALS OF ENGINEERING, STEAM-ENGINES AND BOILERS. 


Oe Te hiene REE 12m0, 
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* id ES ae ADE CORE OM ares WoO 25 alens Tian oes 8vo, 
Bemis, WTI les ATIG RECIPES TA en POE ad stere dd stelt I2mo, 
Carpenters Experimental Engineering. 2°. 67 isk bie Sa onl atsu dee bee a a8 8vo, 
Elena andeventtlatine Buildings: te... Sele erase Wee atedsenterads 8vo, 
Cary’s Smoke Suppression in Plants using Bituminous Coal. (In Prepara- 
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SOGOU se erbanuahotsDraming. . Vuren suse oosten nek ain «3 8vo, paper, 
Coolidge and Freeman’s Elements of General Drafting for Mechanical En- 
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Cromwelks Lreatise on Toothed Gearidg............ nee ereen I2mo, 
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Flather’s Dynamometers and the Measurement of Power............. I2mo, 
Wanda DIOR oe ea aa EN 12mo, 
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Hering’s Ready Reference Tables (Conversion Factors). ..... 16mo, morocco, 
ERE Oe ASL EOC. wc ren ese es ba dsiev seen bees NE ae 8vo, 
SERIES BLES UATE UTA WANG, «ene eeen eene eeens eee ent 8vo, 
Jones’s Machine Design: 
Ranimskinemattcs of Machinery... tn sane ee wo eee sen sites es 8vo, 
Part II. Form, Strength, and Proportions of Parts............... 8vo, 
Kent's Mechanical Engineers’ Pocket-book................ 16mo, morocco, 
eure Pawerand Power Transmission, nt or noren te hoje 3,0) 0 ens nale lens 8vo, 
Leonard’s Machine Shop, Tools, and Methods. ................... 8vo, 
* Lorenz’s Modern Refrigerating Machinery. (Pope, Haven, and Dean.)..8vo, 
MacCord’s Kinematics; or Practical Mechanism. .................... 8vo, 
Wie CNA INO AMS ESCA UUITIO fy-< oisietc En EA AE ER TA Ato. 
vi EE EEE es Be 8vo, 


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MacFarland’s Standard Reduction Factors for Gases, . ..24 STROE 8vo, 


Mahan’s Industuial Drawing. (Thompson.). … sow ae 8vo, 
Poole’s Calorific Power of Fuel’, 0.445... bse 8vo, 
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Richard's Compressed Air, 20.00) LYS) Og I2mo, 
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Wolff's Windmill as a Prime Mover... uus eeen ey, NA 8vg, 
Wood's Turbines, . 2.205... luavaaut. ast vat 8vo, 


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* Bovey’s Strength of Materials and Theory of ‘Structures. 47, eee 8vo, 
Burr’s Elasticity and Resistance of the Materials of Engineering. 6th Edition. 
Reset... „rnc derde Nn 8vc, 
Church’s Mechanics of Engineering, „ass 8vo, 
* Greene’s Structural Mechanics... Siet ee ee 8vo, 
Johnson’s Materials of Construction... … 8vo, 
deep s Cast Inoue ne sE en geeen eee ee en 8vo, 
Lanza’s Applied Mechanics. ............ OENE os eg ee 8vo, 
Martens’s Handbook on Testing Materials. (Henning.)............... 8vo, 
Maurer’s Technical Mechanics, .....,.,.ue0).0 En GVO 
Merriman’s Mechanics of Materials... … peten nr eenn REN 8vo, 
Strength of Materials „ste gens oe I2mo, 
Metcalf’s Steel. A manual for Steel-users......................... I2mo, 
Sabin’s Industrial and Artistic Technology of Paints and Varnish........ 8vo, 
Smith's Materials of Machines... I2mo, 
Thurston’s Materials of Engineering. nere id denn MON 3 vols., 8vo, 
Part Il. Iron and Steel, …. sss 8vo, 
Part III. A Treatise on Brasses, Bronzes, and Other Alloys and their 
Constituents. ne bape 8vo, 
Text-book of the Materials of Construction... 8vo, 
Wood’s (De V.) Treatise on the Resistance of Materials and an Appendix on 
the Preservation of Timber, «eren 8vo, 
Elements of Analytical Mechanics. ........ ak wh een 8vo, 
Wood’s (M. P.) Rustless Coatings: Corrosion and Electrolysis of Iron and 
Steel. . …… „arn, abies oren site neen Jats d SMe Rca AVD, 


Carnot’s Reflections on the Motive Power of Heat. (Thurston.),.. . .I2mo, 
Dawson’s “Engineering” and Electric Traction Pocket-book....16mo mor., 


Ford’s Boiler Making for Boiler Makers............................ 18mo, 
Goss’s Locomotive Sparks. ................. 05454 8vo, 
Hemenway’s Indicator Practice and Steam-engine Economy.......... I2mo, 


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Hutton’s Mechanical Engineering of Power Plants. ............0eeeee> 8vo, 
Bentan deeatsenplnes oi) os ee Mel Iw el es 8vo. 
Tee Tet NOMereMCOMOIDVs > oa ce Fad ardea dees 8vo, 
Kueasss eractice and Theory of the Injector..........0ceecceccscecees 8vo, 
nst NEGEER en 8vo, 
Meyer’s Modernivocomotive Construction. 6a. sort oven ecco bles eee. 4to, 
Peabody’s Manual of the Steam-engine Indicator.................... f2mo. 
Tables of the Properties of Saturated Steam and Other Vapors ..... 8vo, 
Thermodynamics of the Steam-engine and Other Heat-engines...... 8vo, 
Valve-cearsson steam-englnes. RIA Ws oa TEES eee vee 8vo, 
menpody and Miller's Steami-bollers. }; …. fe ee oee eee ees 8vo, 
Pray’s Twenty Years with the Indicator........... ..... ASRAS SSA Large 8vo, 
Pupin’s Thermodynamics of Reversible Cycles in Gases and Saturated Vapors. 
MOSLELNELOD REK ED SE Ua ys ee eS Ay I2mo, 
Reagan’s Locomotives: Simple Compound, and Electric............. 12m0, 
Rontgen’s Principles of Thermodynamics. (Du Bois.). ….............. 8vo, 
Sinclair’s Locomotive Engine Running and Management............. I2mo, 
Smart’s Handbook of Engineering Laboratory Practice............... I2mo, 
BRewiesteamsboilersPractice.. ted AAST ek bos ce oes Adsense ds 8vo, 
Ee EEL EEE A chere w eae 8vo, 
NSO HEEM OA VUANMLB per a tel PRE DN ZE occa eee I2mo, 
Spangler, Greene, and Marshall’s Elements of Steam-engineering....... 8vo, 
Bh asesSteant-BUIDIMES >... aso arden ed re dese ee 8vo, 
PPIs tees EEEN re CEA AE 6 see 8vo, 
Meelrotbhelstealn=eneine., …… Arse side ce oleh eg sce ede 2 vols., 8vo, 
Paroles History, structure „and-Theory: ee de. ee eeen seen 8vo, 
Part II. Design, Construction, and Operation.................... 8vo, 
Handbook of Engine and Boiler Trials, and the Use of the Indicator and 
AD id NE RE te re eae ees ose ee ce cca bess eae 8vo, 
PEO CY) SPP ATM ERC A EE 8vo, 
Steam-boiler Explosions in Theory and in Practice .............. I2mo, 
Manual of Steam-boilers, their Designs, Construction, and Operation..... 8vo, 
Wehrenfenning’s Analysis and Softening of Boiler Feed-water (Patterson) 8vo, 
Weisbach’s Heat, Steam, and Shee mene ae: (Dir Boist\s. 7. nt eee 8vo, 
Waltham soteam—encine Design fifi. St. fies. liad Poe. 8vo, 
Wood’s Thermodynamics, Heat Motors, and Refrigerating Machines. ..8vo, 

MECHANICS AND MACHINERY. 
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* Bovey’s Strength of Materials and Theory of Structures ............. 8vo, 
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Ohneetesechantessofe PACIMRErINg: nr 5 Heuer stol ellni re wek ile AOS 8vo, 
NotessandsExamples in Mechanics. . 5. raars ME Jer lar dle dist wears 8vo, 
‘Compton’s First Lessons in Metal-working................... Tis eal2Inos 
Compton. and De Groodt’s The Speed Lathe..............ccedeceens I2mo, 
Cromwell's Treatise on Loothed Gearing... sica whi Need Heelers I2mo, 
rieatselonsBeltstandPalleys. sterven. en tee ese ee de I2mo, 
Dana’s Text-book of Elementary Mechanics for Colleges and Schools. .12mo, 
Ditseyre machineryrrattern Making | 2). Pee dee cies I2mo, 
Dredge’s Record of the Transportation Exhibits Building of the World’s 
Columbian Exposition of 180365066. os. oe oe ie 4to half morocco, 

u Bois’s Elementary Principles of Mechanics: 

EERE 0 Lath hue ses dede dae an ate oe 8vo, 
EEND Weele daarden ev monde RAE TAS 8vo, 
Mechanicsrot Pnpineering. Vol. ‘Teens. tees wenen ede Small 4to, 
OPEN Boats oh ane Pie EU de ar Small 4to, 
enen minematics of Machines... ….…..: ies icdacccorncebecdccuces 8vo, 


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Fitzgerald’s Boston Machinist. .. sont Vans. on). rete ee 16mo, 
Flather’s Dynamometers, and the Measurement of Power............ I2mo, 
Rope Driving. .....,0.6.-,0.0.c.c00. oo eomectie 5 aon ete 91057 see I2mo, 
Goss’s Locomotive Sparks, 0.7%. |: . onee ale base: Be EE EE 8vo, 
* Greene’s Structural Mechanics: ,, . „00e en ee ee En .8vo, 
Hall’s Car Lubrication... ese ve wie ele ee eee ee I2mo, 
Holly’s Art of Saw Filing... . ys Wurghins tora Ste ee eee ne 18mo, 
James’s Kinematics of a Point and the Rational Mechanics of a Particle. 
Smail 8vo, 
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Johnson’s (L. J.) Statics by Graphic and Algebraic Methods. ....... ai. 2 8vo; 
Jones’s Machine Design: 
Part 1. Kinematics of Machinery: ete ciao eee 8vo, 
Part II. Form, Strength, and Proportions of Parts............... 8vo, 
Kerr’s Power and Power Transmission: tse 9. ae pe) ese 8vo, 
Lanza’s Applied Mechanics: ……srrtd „ooch! ee sten denn ae Sl 8vo, 
Leonard’s Machine Shop, Tools, and Methods.....................+-.. 8vo, 
* Lorenz’s Modern Refrigerating Machinery. (Pope, Haven, and Dean.).8vo, 
MacCord’s Kinematics; or. Practical Mechanism. .................... 8vo, 
Velocity Diagrams. ... «+... 225+: ede eN 8vo, 
* Martin’s Text Book on Mechanics, Vol. I, Statics................. I2mo, 
Maurer’s Technical Mechanics: cit Sis tetten een 8vo, 
Merriman’s Mechanics of Materials... Jo. oe «eles onee 8vo, 
* Elements of Mechanics... „alie oe se cus Wenne EE I2mo, 
* Michie’s Elements of Analytical Mechanics..................... .. .8V0, 
* Parshall and Hobart’s Electric Machine Design............ Ato, half morocco, 1 
Reagan’s Locomotives: Simple, Compound, and Electric............. 12mo, 
Reid’s Course: in: Mechanical Drawing... st see oe eee 8vo, 
Text-book of Mechanical Drawing and Elementary Machine Design.8vo, 
Richards’s Compressed Air... ….…. ooo J's ou nan eee 12 m0, 
Robinson’s. Principles of Mechanism. nn. « Hensen sn stee eee 8vo, 
Ryan, Norris, and Hoxie’s Electrical Machinery. Vol.I............... 8vo, 
Sanborn’s. Mechanics: Problems... £ „ar vak 6... os See Large I2mo, 
Schwamb and Merrill’s Elements of Mechanism... ............+..++-- 8vo, 
Sinclair’s Locomotive-engine Running and Management... .......... 1210, 
Smith’s (O.) Press-working of Metals ..............eee eneen eneen 8vo, 
Smith’s (A. W.) Materials of Machines... ‚natste oee ee emp eee I2mo, 
Smith (A. W.) and Marx’s Machine Design... .............+.+--+-0-: 8vo, 
Spangler, Greene, and Marshall’s Elements of Steam-engineering........ 8vo, 
Thurston’s Treatise on Friction and Lost Work in Machinery and Mili 
Work. … . cece cc cnss bee ov ess oes) e eels ates _..8vo, 
Animalas a Machine and Prime Motor, and the Laws of Energetics. 12mo, 
Warren’s Elements of Machine Construction and Drawing............. 8vo, 
Weisbach’s Kinematics and Power of Transmission. (Herrmann—Klein.).8vo, 
Machinery of Transmission and Governors. (Herrmann—K ‘sin.).8vo, 
Wood’s Elements of Analytical Mechanics. ............es eene eenen nen 8vo, 
Principles of Elementary Mechanics... ...... sees eeen eneen r2mo, 
Turbines. … 65455 26 Shs bP ae nes SVO, 
The World's Columbian Exposition of 1893 ... ....seseestseeeeeeeneer 4to, 
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** Tles’s Lead-smelting. (Postage o cents additional.)..............-- I2mo, 
Keep’s Cast Iron, 5.0544 sie a ase © See bs deoewidtamdaioror 


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Kunhardt’s Practice of Ore Dressing in Europe... .…................…. 8vo, I 50 
Le Chatelier’s High-temperature Measurements. (Boudouard—Burgess.)12m0. 3 oo 
Metcalf’s Steel. A Manual for Steel-users. .. .……..................…. I2mo, 2 O0 
PREVI VETIC CPE LOCOSE Mth cts) f a cee Sadr) di iw ow eee oa TE asta ob I2mo, I 00 
Minet’s Production of Aluminum and its Industrial Use. (Waldo.)....12m0, 2 50 
Robine and Lenglen’s Cyanide Industry. (Le Clerc.)................. 8vo, 4 00 
Tk EM EN ENA LEV Ne c.c.c.. 5. 5 6 ood oo ae! sep pd aiehal «ndaelend elovele ees I2mo, I 00 
Thurston’s Materials of Engineering. In Three Parts. ................ 8vo, 8 oo 
ieder Mdd ON A 8vo, 3 50 

Part III. A Treatise on Brasses, Bronzes, and Other Alloys and their 
(MOTE EN CECE: os BS iy eae) ee 8vo, 2 50 
Ulke’s Modern Electrolytic Copper Refining.................0ceeceees 8vo, 3 00 

© 
MINERALOGY. 

Barringer’s Description of Minerals of Commercial Value. Oblong, morocco, 2 50 
Boyd’s Resources of Southwest Virginia. ............ 0.0... 0.0. cc eee 8vo, 3 00 
Maniot SOmtinwestwVITIONIA.. nende Pocket-book form. 2 oo 
Brush’s Manual of Determinative Mineralogy. (Penfield.)............. 8vo, 4 00 
Pama otalouwe of Minerals... „ariel odes Meden ies ees 8vo, paper, I 00 
Cloth, 25 
Dicuonary otune Names of Minerals. 5.4... eeen. 8vo 3 50. 
Mana’siaystem of Mineralogy: .. 50... 6c eee wee eae Large 8vo, half leather 12 50 
First Appendix to Dana’s New ‘‘ System of Mineralogy.’’..... Large 8vo, 1 oo 
emt DOOk CreMIINelaAlO sol ont Ans ARENA eee vla ele eee ls Ohl 8vo, 4 00 
NhaeralssardsHlowsto Study Them... odie oc ewe eee nd I2mo, I 50 
Catalogue of American Localities of Minerals............... Large 8vo, 1 oo 
Manual of Mineralogy and Petrography...................-00-- T2M0, 200 
Douglas’s Untechnical Addresses on Technical Subjects.............. I2mo, I 00 
rt ME CT ATMO NE MN os Able wea Ef 8vo, "1 25 
Egleston’s Catalogue of Minerals and Synonyms...................... 8vo, 2 50 
Goesel‘s Minerals and Metals: A Reference Book.. ........... 16mo,mMor.. 3 oo 
Groth’s Introduction to Chemical Crystallography (Marshall)........ 12M6,* tf 25 
Hussak’s The Determination of Rock-forming Minerals. (Smith.).Small 8vo, 2 oo 
Merrill’s Non-metallic Minerals: Their Occurrence and Uses.......... 8vo, 4 00 

* Penfield’s Notes on Determinative Mineralogy and Record of Mineral Tests. 
8vo, paper, 50. 

Rosenbusch’s Microscopical Physiography of the Rock-making Minerals. 
EEEN MOES ONE cao ANN tied PANE“ Et EFTA 8vo, 5 oa 
* Tillman’s Text-book of Important Minerals and Rocks. .............. 8vo, 2 00 

MINING. 

Beard’s Ventilation of Mines. ................... > ERE I2M0, 2 50 
Boyd’s Resources of Southwest Virginia. ........... AG As ER See 8vo, 3 00 
Mapsotssoutbwest. Wil INIA)... Sansa esi Pocket-book form, 2 oo 
Douglas’s Untechnical Addresses on Technical Subjects. . ............ I2mo, I O0 
* Drinker’s Tunneling, Explosive Compounds, and Rock Drills. .4to, hf. mor., 25 oo 
Bissler sModernikieh ExplosiVes: aktentas Horses waste hets t Wetzel 873 4 CO 
Goesel’s Minerals and Metals: A Reference Book.. .......... 16mo, mor. 3 oo 
Goodyear’s Coal-mines of the Western Coast of the United States...... I2mo, 2 50 
Misano Wanita lof Wifi’... an Waer Zeal k Hete art ant lea 8vo, 5 00 
** Tles’s Lead-smelting. (Postage gc. additional.), .................. I2mo, 2 50 
Kunhardt’s Practice of Ore Dressing in Europe. .............0.000000: 8vo; I 50 
Met ee EE PERCEEL en renee de WAR FORA I2mo, I 00 


‘O’Driscoll’s Notes on the Treatment of Gold Ores. ............. REBEL 


Robine and Lenglen’s Cyanide JOUE, (Le Clerc, ), nn an 8vo, 
* Walke's Lectures on Explosives,;.: 2.77.0... .. ee 8vo, 
"Weaver's Military Explosives,, …. 5. ini 5) 2°? 205 8vo, 
Wilson's Cyanide Processes.) eten I2mo, 
Chlorination Protess- A0, 0i 0. os csc coe a oe a ae I2mo, 
Hydraulic and Placer Mining. …. nessen (ee I2mo, 
Treatise on Practical and Theoretical Mine Ventilation........... 12 mo, 


SANITARY SCIENCE. 


Bashore’s Sanitation of a Country House............. EEEN a -I2mo, 
* Outlines of Practical Sanitation. …… … „or 0. ee I2mo, 
Folwell’s Sewerage. (Designing, Construction, and Maintenance. ). . .8vo, 
Water-supply Engineering, „sn oven ot oeheune eae na 8vo, 
Fowler’s Sewage Works Analyses... van Ja saatn Boedie vs Une eee 1219, 
Fuertes’s Water and Public Health.................. EE Brae se Moe suis. I2mo, 
Water-filtration Works, «0.00... ar aren ce Ree ee ee I2mo, 
Gerhard’s Guide to Sanitary House-inspection...................... 16mo, 
Goodrich’s Economic Disposal of Town’s Refuse................ Demy 8vo, 
Hazen’s Filtration of Public Water-supplies.......................... 8vo, 
Leach’s The Inspection and Analysis of Food with Special Reference to State 
Controle... 4, ante oon oven vara nn 8vo, 

Mason’s Water-supply. (Considered principally from a Sanitary Standpoint) 8vo, 
Examination of Water. (Chemical and Bacteriological.)......... I2mo, 
Ogden’s Sewer Design. . 2. sn aan SA I2mo, 
Prescott and Winslow’s Elements of Water Bacteriology, with Special Refer- 
ence to Sanitary Water Analysis. «vat ve e.g eee I2mo, 

* Price’s Handbook on Sanitation, . -.)- Jou.) 7. 54 ee I2mo, 
Richards’s Cost of Food. A Study in Dietaries. „ann 7.20 I2mo, 
Costsof Living as Modified by Sanitary Science.................. I2mo, 
Cost of Shelter... ,...: .... oct. osu ee hee oe ee I2mo, 
Richards and Woodman’s Air, Water, and Food from a Sanitary Stand- 
point... „tnt. lk, Bee ia a ee 8vo, 

* Richards and Williams’s The Dietary Computer, ...4 79049), ALE 8vo, 
Rideal’s Sewage and Bacterial Purification of Sewage. AERON RDE a 8vo, 
Turneaure and Russell's Public Water-supplies. 8vo, 
Von Behring’s Suppression of Tuberculosis (Bolduin Jed I2mo, 
‘Whipple’s Microscopy of Drinking-water...........sseeeceeeeeels 8vo, 
Winton’s Microscopy of Vegetable Foods. . ….... 8vo, 
‘Woodhull’s Notes on Military Hygiene. .................. erde te we RO EOIN 
vk Personal Hygiene........... sort ano. cede oe ) Sa ae I2mo, 

MISCELLANEOUS. 

De Fursac’s Manual of Psychiatry. (Rosanoff and Collins. )....Large 12mo, 
Ehrlich’s Collected Studies on Immunity (Bolduan) {927-)-) 8vo, 
Emmons’s Geological Guide-book of the Rocky Mountain Excurston of the 
International Congress of Geologists. .. Large 8vo, 

Ferrel’s Popular Treatise on the Winds................. htt 8vo. 
Haines’s American Railway Management. ............... reren. I2mo, 
Mott’s Fallacy of the Present Theory of. Sound sanne .16mo, 
Ricketts’s History of Rensselaer Polytechnic Institute, zBa4 Boll Small 8vo, 
Rostoski’s Serum Diagnosis. (Bolduan.). ea en TTN 


Rotherham’s Emphasized New Testament... ............e..... . Large 8vo, 


18 


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Steel’s Treatise on the Diseases or the Dog..... 2... ccc cece cecccccecee 8vo, 


Weerwoord sColamlbiansxposition of T803 . teer inenen Ato, 
Von Behring’s Suppression of Tuberculosis. (Bolduan.)............. I2mo, 
Winslow’s Elements of Applied Microscopy............./.......05- I2mo, 


Worcester and Atkinson. Small Hospitals, Establishment and Maintenance; 
Suggestions for Hospital Architecture: Plans for Small Hospital. 12mo, 


HEBREW AND CHALDEE TEXT-BOOKS. 


Green’s Elementary Hebrew Grammar................0cccccccccees I2mo, 
BIC eae IGE RCOMM ATL a). are cies clo is ow Gslele esl ate ccs ee se este sna 8vo, 
Gesenius’s Hebrew and Chaldee Lexicon to. the Old Testament Scriptures. 
NEEN en ee dee ele vc w deed Small 4to, half morocco, 
Letteris’s Hebrew Bible.. .................. RN REA 8vo, 


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